Trifluoro-methanesulfonic acid (2S,3R)-3-heptyl-oxiranylmethyl ester | 134680-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Trifluoro-methanesulfonic acid (2S,3R)-3-heptyl-oxiranylmethyl ester
• CAS: 134680-33-4
• 化学式: C₁₁H₁₉F₃O₄S
• 分子量: 304.331
• InChiKey: NUOJRAKMPVOMKU-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2S,3R)-3-heptyl-oxiranylmethyl ester 在 甲醇 、 正丁基锂 、 盐酸羟胺 、 potassium carbonate 、 正丁胺 、 copper(l) chloride 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 7.58h， 生成 (3S,9S,10R)-panaxydol
  参考文献：
  名称：

  Total synthesis of panaxydol and its stereoisomers as potential anticancer agents

  摘要：

  An efficient total synthesis of natural panaxydol la and its seven stereoisomers 1b-h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.12.001
• 作为产物：
  描述：

  (Z)-2-decen-1-ol 在 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 癸烷 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 Trifluoro-methanesulfonic acid (2S,3R)-3-heptyl-oxiranylmethyl ester
  参考文献：
  名称：

  Total synthesis of panaxydol and its stereoisomers as potential anticancer agents

  摘要：

  An efficient total synthesis of natural panaxydol la and its seven stereoisomers 1b-h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.12.001

文献信息

• Total synthesis and absolute stereochemistry of (9R,10S)-epoxyheptadecan-4,6-diyn-3-one, a diacylglycerol acyltransferase inhibitor from Panax ginseng
  作者：Jung-Hoon Oh、Hyun Sun Lee、Mun-Chual Rho、Young Kook Kim、Hyeong Kyu Lee、Woo Song Lee、Jae Nyoung Kim、Sangku Lee、Sang-Hun Jung

  DOI：10.1016/j.tetlet.2004.07.153

  日期：2004.9

  Asymmetric synthesis of four possible stereoisomers of (9,10) -epoxyheptadecan-4,6-diyn-3-one was accomplished, and the absolute configuration of the naturally occurring (9R,10S)-epoxyheptadecan-4,6-diyn-3-one (1) was elucidated. (C) 2004 Elsevier Ltd. All rights reserved.