(S,Z)-methyl 17-hydroxyoctadece-9-enoate | 114127-64-9

• 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: (S,Z)-methyl 17-hydroxyoctadece-9-enoate
• 英文别名: methyl 17-hydroxyoleate；17-Hydroxy-cis-9-octadecensaeure-methylester；methyl (Z,17S)-17-hydroxyoctadec-9-enoate
• CAS: 114127-64-9
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: YFBTWGWAXOETRB-JXCVUKRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,Z)-methyl 17-hydroxyoctadece-9-enoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 17-羟基油酸
  参考文献：
  名称：

  槐糖脂衍生的多羟基脂肪酸

  摘要：

  AbstractStarting from 17‐hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups can be incorporated in the C18 chain in a variety of geometries, for example spaced widely throughout the chain at C1, C8, and C17. This regiochemical control will be of use in structure/function studies involving materials constructed from these hydroxy fatty acids. A further benefit is that the hydroxy groups can be present in protected or free states. The principal reactions used to introduce extra hydroxy groups are selenium oxide‐mediated allylic hydroxylation, osmium‐catalyzed dihydroxylation, and borohydride reduction of a carboxylic ester. These new compounds are expected to be of use in a number of areas, but particularly as building blocks for polymers or components of lubricant formulations.

  DOI：

  10.1007/s11746-007-1054-4
• 作为产物：
  描述：

  7-溴-1-庚烯 在 C₃₅H₄₇N₃O₄Ru 、 碘 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (S,Z)-methyl 17-hydroxyoctadece-9-enoate
  参考文献：
  名称：

  Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

  摘要：

  (R)-Harmonine 是以 Z 选择性交叉甲基化反应为核心，通过六步顺序合成的，总收率为 15%。通过这种策略，目标物中的顺式烯烃可以被完全安装。使用醇和酯作为胺前体对于从自甲氧基化产物中分离出交叉甲氧基化产物至关重要。这种方法还被用于制备两种新型的哈蒙德碱类似物。

  DOI：

  10.1071/ch15397

文献信息

• HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE
  作者：P. A. J. Gorin、J. F. T. Spencer、A. P. Tulloch

  DOI：10.1139/v61-104

  日期：1961.4.1

  The oil formed during fermentation by a strain of Torulopsismagnoliae consisted mainly of partly acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units attached β-glycosidically to 17-L-hydroxyoctadecanoic and 17-L-hydroxy-9-octadecenoic acids.

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。
• Access to harmonine, a chemical weapon of ladybird beetles
  作者：Satish Chandra Philkhana、Prabhu Dhasaiyan、B. L. V. Prasad、D. Srinivasa Reddy

  DOI：10.1039/c4ra05859c

  日期：——

  The synthesis of harmonine, a defense alkaloid from the harlequin ladybird is reported by three different routes.

  报道了三种不同的途径合成彩衣瓢虫防御性生物碱——哈莫宁的方法。
• Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst
  作者：Steven-Alan G. Abel、Wesley J. Olivier、Richard L. Pederson、Alex C. Bissember、Jason A. Smith

  DOI：10.1071/ch15397

  日期：——

  (R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

  (R)-Harmonine 是以 Z 选择性交叉甲基化反应为核心，通过六步顺序合成的，总收率为 15%。通过这种策略，目标物中的顺式烯烃可以被完全安装。使用醇和酯作为胺前体对于从自甲氧基化产物中分离出交叉甲氧基化产物至关重要。这种方法还被用于制备两种新型的哈蒙德碱类似物。
• Polyhydroxy Fatty Acids Derived from Sophorolipids
  作者：Jonathan A. Zerkowski、Daniel K. Y. Solaiman

  DOI：10.1007/s11746-007-1054-4

  日期：2007.5.10

  AbstractStarting from 17‐hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups can be incorporated in the C18 chain in a variety of geometries, for example spaced widely throughout the chain at C1, C8, and C17. This regiochemical control will be of use in structure/function studies involving materials constructed from these hydroxy fatty acids. A further benefit is that the hydroxy groups can be present in protected or free states. The principal reactions used to introduce extra hydroxy groups are selenium oxide‐mediated allylic hydroxylation, osmium‐catalyzed dihydroxylation, and borohydride reduction of a carboxylic ester. These new compounds are expected to be of use in a number of areas, but particularly as building blocks for polymers or components of lubricant formulations.