甲基2-氟棕橘酸盐 | 137676-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基2-氟棕橘酸盐
• 英文名称: methyl 2-fluorohexadecanoate
• CAS: 137676-82-5
• 化学式: C₁₇H₃₃FO₂
• 分子量: 288.446
• InChiKey: RTABFVHVABARDD-UHFFFAOYSA-N

物化性质

• 沸点：
  304.8±10.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基十六烷酸甲酯 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以78%的产率得到甲基2-氟棕橘酸盐
  参考文献：
  名称：

  2-oxothiazole compounds and method of using same for chronic inflammatory disorders

  摘要：

  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。

  公开号：

  US09597318B2

文献信息

• 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。
• Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes
  作者：Constantinos Baskakis、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm800649q

  日期：2008.12.25

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.
• 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.
• US9597318B2
  申请人：——

  公开号：US9597318B2

  公开（公告）日：2017-03-21