2-fluorohexadecanal | 156185-03-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2-fluorohexadecanal
• CAS: 156185-03-4
• 化学式: C₁₆H₃₁FO
• 分子量: 258.42
• InChiKey: VSZOVRHQNWNNFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-fluorohexadecanal 在 甲基磺酰胺 、 AD-mix-β 、 sodium hydride 作用下， 以 乙醚 、 水 、 叔丁醇 为溶剂， 反应 172.0h， 生成 ethyl (2S,3S)-4-fluoro-2,3-dihydroxyoctadecanoate
  参考文献：
  名称：

  非对映体 4-氟-4,5-二氢神经酰胺的两种对映体的合成

  摘要：

  两种非对映异构体对映体纯 4-氟-4,5-二氢神经酰胺在 2-和 3-碳原子处具有天然 D-赤型构型，以对映选择性的 11 步序列合成。合成的关键步骤是将 trans-4-fluorooctadec-2-enoate (8) 乙基 trans-4-fluorooctadec-2-enoate (8) 与 AD-mix-β 进行非对映选择性不对称 Sharpless 二羟基化，以提供 D-erythro 排列。使用 AD-mix-α 类似地合成其他对映体系列的非对映异构体。在所有情况下，通过环硫酸盐 13 和 14 与叠氮化物的区域和立体选择性开环，氮杂原子被引入到 2 位。Staudinger 还原，中间形成的氨基的酰化，非对映异构体的色谱分离和酯官能团在甲醇存在下用硼氢化钠化学选择性还原得到两种对映纯形式的标题化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA

  DOI：

  10.1002/ejoc.200600456
• 作为产物：
  描述：

  十六碳烯 生成 2-fluorohexadecanal
  参考文献：
  名称：

  非对映体 4-氟-4,5-二氢神经酰胺的两种对映体的合成

  摘要：

  两种非对映异构体对映体纯 4-氟-4,5-二氢神经酰胺在 2-和 3-碳原子处具有天然 D-赤型构型，以对映选择性的 11 步序列合成。合成的关键步骤是将 trans-4-fluorooctadec-2-enoate (8) 乙基 trans-4-fluorooctadec-2-enoate (8) 与 AD-mix-β 进行非对映选择性不对称 Sharpless 二羟基化，以提供 D-erythro 排列。使用 AD-mix-α 类似地合成其他对映体系列的非对映异构体。在所有情况下，通过环硫酸盐 13 和 14 与叠氮化物的区域和立体选择性开环，氮杂原子被引入到 2 位。Staudinger 还原，中间形成的氨基的酰化，非对映异构体的色谱分离和酯官能团在甲醇存在下用硼氢化钠化学选择性还原得到两种对映纯形式的标题化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA

  DOI：

  10.1002/ejoc.200600456

文献信息

• 2-oxothiazole compounds and method of using same for chronic inflammatory disorders
  申请人：Kokotos George

  公开号：US09597318B2

  公开（公告）日：2017-03-21

  The invention provides compounds of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond, —O—, or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  该发明提供了以下式（I）的化合物，其中X为O或S；R1为H、OH、SH、硝基、NH2、NHC1-6烷基、N（C1-6烷基）2、卤素、卤代C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON（C1-6烷基）2、OCOC1-6烷基，或者是酸性基团，例如包含羧基、磷酸基、磷酸酯基、硫酸基、磺酸基或四唑基团的基团；R2如R1定义或R1和R2一起形成一个6-成员芳香环，可选地由多达4个R5基团取代；R3为H、卤素（优选氟素），或CHal3（优选CF3）；每个R5如R1定义；V1为共价键，—O—，或C1-20烷基，或C2-20单烯或多不饱和烯基；所述烷基或烯基基团可选地由O、NH、N（C1-6烷基）、S、SO或SO2中选择的一个或多个杂原子中断；M1不存在或为C5-10环烷基或C5-15芳基；R4为H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N（C1-6烷基）2、卤代C1-6烷基、C1-20烷基，或C2-20单烯或多不饱和烯基，所述C1-20烷基或C2-20烯基基团可选地由O、NH、N（C1-6烷基）、S、SO或SO2中选择的一个或多个杂原子中断；但条件是，V1M1R4作为一个整体至少提供来自C（R3）基团的4个骨架原子；或其盐、酯、溶剂化合物、N-氧化物或前药；用于治疗慢性炎症症状。
• Stereoselective Synthesis of Fluorinated and Nonfluorinated Triazolo Analogues of Ceramides
  作者：Günter Haufe、Katarzyna Koroniak

  DOI：10.1055/s-0029-1218591

  日期：2010.2

  prepared enantioselectively. Key steps of the synthetic sequence are asymmetric Sharpless dihydroxylation of α,β-unsaturated esters to diols, regioselective ring opening of derived cyclic sulfates by azide, 1,3-dipolar cycloaddition with alkynes, and reduction of the ester groups. sphingolipids - asymmetric synthesis - 1,3-dipolar cycloaddition - triazoles - enantioselective fluorination - nucleophilic

  对映体选择性地制备了一系列天然存在的鞘脂的非对映异构的氟化和非氟化的三唑类似物，例如二氢神经酰胺，适用于物理化学和药物化学应用。合成序列的关键步骤是α，β-不饱和酯向二醇的不对称Sharpless二羟基化，叠氮化物衍生的环状硫酸盐的区域选择性开环，炔烃与1,3-偶极环加成反应以及酯基的还原。 鞘脂-不对称合成-1,3-偶极环加成-三唑-对映选择性氟化-亲核取代
• ANTIINFLAMMATORY 2-OXOTHIAZOLES
  申请人：Avexxin AS

  公开号：EP3431084A1

  公开（公告）日：2019-01-23

  A compound of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  式 (I) 的化合物 其中 X 是 O 或 S； R1是H、OH、SH、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤素、卤代 C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON(C1-6烷基)2、OCOC1-6烷基或酸性基团，如包含羧基、磷酸基、膦酸 基、硫酸基、磺酸基或四唑基的基团； R2 如 R1 所定义，或 R1 和 R2 可共同形成一个最多被 4 个基团 R5 任选取代的 6 元芳香环； R3 是 H、卤代（最好是氟代）或 CHal3（最好是 CF3）； 每个 R5 的定义与 R1 相同； V1 是共价键或 C1-20 烷基或 C2-20 单不饱和或多不饱和烯基；所述烷基或烯基任选被选自 O、NH、N（C1-6 烷基）、S、SO 或 SO2 的一个或多个杂原子所取代； M1 不存在或为 C5-10 环状基团或 C5-15 芳香基团；以及 R4 是 H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤代 C1-6烷基、C1-20烷基或 C2-20 单不饱和或多不饱和烯基，所述 C1-20 烷基或 C2-20 烯基任选被一个或多个选自 O、NH、N(C1-6烷基)、S、SO 或 SO2 的杂原子间隔； 但整个基团 V1M1R4 至少有 4 个来自 C（R3）基团的骨架原子； 或其盐、酯、溶剂、N-氧化物或原药； 用于治疗慢性炎症。
• ANTI INFLAMMATORY 2-OXOTHIAZOLES AND 2 -OXOOXAZOLES
  申请人：Avexxin AS

  公开号：EP2482815A1

  公开（公告）日：2012-08-08
• COMPOUND
  申请人：Kokotos George

  公开号：US20110136879A1

  公开（公告）日：2011-06-09

  The invention provides compounds of formula (I) wherein X is O or S; R 1 is H, OH, SH, nitro, NH 2 , NHC 1-6 alkyl, N(C 1-6 alkyl) 2 , halo, haloC 1-6 alkyl, CN, C 1-6 -alkyl, OC 1-6 alkyl, C 1-6 alkylCOOH, C 1-6 alkylCOOC 1-6 alkyl, C 2-6 -alkenyl, C 3-10 cycloalkyl, C 6-10 aryl, C 1-6 alkylC 6-10 aryl, heterocyclyl, heteroaryl, CONH 2 , CONHC 1-6 alkyl, CON(C 1-6 alkyl) 2 , OCOC 1-6 alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R 2 is as defined for R 1 or R 1 and R 2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R 5 ; R 3 is H, halo (preferably fluoro), or CHal 3 (preferably CF 3 ), each R 5 is defined as for R 1 ; V 1 is a covalent bond or a C 1-20 alkyl group, or C 2-20 -mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C 1-6 alkyl), S, SO, or SO 2 ; M 1 is absent or is a C 5-10 cyclic group or a C 5-15 aromatic group; and R 4 is H, halo, OH, CN, nitro, NH 2 , NHC 1-6 alkyl, N(C 1-6 alkyl) 2 , haloC 1-6 alkyl, a C 1-20 alkyl group, or C 2-20 -mono or multiply unsaturated alkenyl group, said C 1-20 alkyl or C 2-20 alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C 1-6 alkyl), S, SO, or SO 2 ; with the proviso that the group V 1 M 1 R 4 as a whole provides at least 4 backbone atoms from the C(R 3 ) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.