3-(Nonyl)dodecan-1-ol | 80256-62-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(Nonyl)dodecan-1-ol
• 英文别名: 3-Nonyldodecan-1-ol
• CAS: 80256-62-8
• 化学式: C₂₁H₄₄O
• 分子量: 312.58
• InChiKey: JTFRIVJFXWNXCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±10.0 °C(Predicted)
• 密度：
  0.837±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(Nonyl)dodecan-1-ol 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到3-nonyldodecyl p-toluenesulfonate
  参考文献：
  名称：

  Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate

  摘要：

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

  DOI：

  10.1021/jm3016443
• 作为产物：
  描述：

  10-十九烷酮 在 palladium on activated charcoal lithium aluminium tetrahydride 、 甲酸 、 氢气 、 mercury dichloride 、 锌 作用下， 以 乙醚 、 苯 为溶剂， 反应 9.0h， 生成 3-(Nonyl)dodecan-1-ol
  参考文献：
  名称：

  Recherches sur les substances mesomorphes—IX

  摘要：

  DOI：

  10.1016/s0040-4020(01)92352-x

文献信息

• Cationic Lipid
  申请人：EISAI R&D MANAGEMENT CO., LTD.

  公开号：US20200308111A1

  公开（公告）日：2020-10-01

  The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1) or a pharmaceutically acceptable salt thereof, wherein L 1 and L 2 independently represent an alkylene group having 3 to 10 carbon atoms; R 1 and R 2 independently represent an alkyl group having 4 to 24 carbon atoms or an alkenyl group having 4 to 24 carbon atoms; R 3 represents an alkyl group having 1 to 3 carbon atoms; and X 1 represents a single bond or CO—O—.

  本发明提供了一种阳离子脂质，可用于将核酸传递至细胞质。根据本发明的一种阳离子脂质，例如，是由式（1）表示的化合物或其药学上可接受的盐，其中L1和L2分别表示具有3至10个碳原子的烷基基团；R1和R2分别表示具有4至24个碳原子的烷基基团或具有4至24个碳原子的烯基基团；R3表示具有1至3个碳原子的烷基基团；X1表示单键或CO—O—。
• CATIONIC LIPID
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP3733647A1

  公开（公告）日：2020-11-04

  The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1) or a pharmaceutically acceptable salt thereof, wherein L1 and L2 independently represent an alkylene group having 3 to 10 carbon atoms; R1 and R2 independently represent an alkyl group having 4 to 24 carbon atoms or an alkenyl group having 4 to 24 carbon atoms; R3 represents an alkyl group having 1 to 3 carbon atoms; and X1 represents a single bond or CO-O-.

  本发明提供了一种可用于将核酸递送至细胞质的阳离子脂质。根据本发明的阳离子脂质是例如由式（1）代表的化合物或其药学上可接受的盐，其中 L1 和 L2 独立地代表具有 3 至 10 个碳原子的亚烷基；R1 和 R2 独立地代表具有 4 至 24 个碳原子的烷基或具有 4 至 24 个碳原子的烯基；R3 代表具有 1 至 3 个碳原子的烷基；X1 代表单键或 CO-O-。
• Cationic lipid
  申请人：EISAI R&D MANAGEMENT CO., LTD.

  公开号：US10947193B2

  公开（公告）日：2021-03-16

  The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1) or a pharmaceutically acceptable salt thereof, wherein L1 and L2 independently represent an alkylene group having 3 to 10 carbon atoms; R1 and R2 independently represent an alkyl group having 4 to 24 carbon atoms or an alkenyl group having 4 to 24 carbon atoms; R3 represents an alkyl group having 1 to 3 carbon atoms; and X1 represents a single bond or CO—O—.

  本发明提供了一种可用于将核酸递送至细胞质的阳离子脂质。 根据本发明的阳离子脂质是例如由式（1）代表的化合物或其药学上可接受的盐，其中 L1 和 L2 独立地代表具有 3 至 10 个碳原子的亚烷基；R1 和 R2 独立地代表具有 4 至 24 个碳原子的烷基或具有 4 至 24 个碳原子的烯基；R3 代表具有 1 至 3 个碳原子的烷基；X1 代表单键或 CO-O-。
• Recherches sur les substances mesomorphes—IX
  作者：Jacques Malthête、Josette Canceill、Jacqueline Gabard、Jean Jacques

  DOI：10.1016/s0040-4020(01)92352-x

  日期：1981.1
• Synthetic Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM₃and GM₄Analogs Containing 2- OR 3-Branched Fatty-Alkyl Residues in Place of Ceramide
  作者：Akira Hasegawa、Naomi Suzuki、Hideharu Ishida、Makoto Kiso

  DOI：10.1080/07328309608005679

  日期：1996.7

  Each of four ganglioside GM(4) and GM(3) analogues containing 2- or 3-branched fatty alkyl residues in place of ceramide have been synthesized. Coupling of O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3) -2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (13) or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-3 -O-acetyl-2,4-di-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (14) with 2- or 3-branched fatty-alkyl-1-ols (9-12), prepared from the corresponding branched fatty acids by methyl esterification and reduction, using BF3 . OEt(2) gave the corresponding ganglioside analogues (15, 17, 19, 21, 23, 25, 27, 29) in good yields, which were coverted, via O-deacylation and de-esterification, into the tide compounds.