Trifluoro-methanesulfonic acid (2R,3S)-3-heptyl-oxiranylmethyl ester | 134645-42-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3S)-3-heptyl-oxiranylmethyl ester
• 英文别名: [(2R,3S)-3-heptyloxiran-2-yl]methyl trifluoromethanesulfonate
• CAS: 134645-42-4
• 化学式: C₁₁H₁₉F₃O₄S
• 分子量: 304.331
• InChiKey: NUOJRAKMPVOMKU-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2R,3S)-3-heptyl-oxiranylmethyl ester 在 N,N-二甲基丙烯基脲 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 Oxone 、 正丁基锂 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.5h， 生成 人参炔E
  参考文献：
  名称：

  Studies towards the Biomimetic Synthesis of Ginsenoyne L; Efficient Synthesis of 2'-epi-Ginsenoyne L

  摘要：

  DOI：

  10.3987/com-02-s25
• 作为产物：
  描述：

  2-癸炔-1-醇 在 吡啶 、 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 氢气 、 D-(-)-酒石酸二异丙酯 作用下， 以 癸烷 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 73.0h， 生成 Trifluoro-methanesulfonic acid (2R,3S)-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

• New Polyacetylenes, DGAT Inhibitors from the Roots of<i>Panax ginseng</i>
  作者：Lee, Seung Woong、Kim, Koanhoi、Rho, Mun-Chual、Chung, Mi Yeon、Kim, Young Ho、Lee, Sangku、Lee, Hyun Sun、Kim, Young Kook

  DOI：10.1055/s-2004-815534

  日期：2004.3

  The petroleum ether extract of Panax ginseng showed a significant inhibition of the diacylglycerol acyltransferase (DGAT) enzyme from rat liver microsomes. Bioactivity-guided fractionation led to the isolation of two new polyacetylenic compounds, (9 R,10 S)-epoxyheptadecan-4,6-diyn-3-one ( 1) and 1-methoxy-(9 R,10 S)-epoxyheptadecan-4,6-diyn-3-one ( 2). Their chemical structures were elucidated on

  人参的石油醚提取物对大鼠肝微粒体的二酰基甘油酰基转移酶（DGAT）酶具有显着抑制作用。生物活性指导的分馏导致分离出两种新的聚炔化合物，（9 R，10 S）-环氧庚烷-4,6-diyn-3-one（1）和1-甲氧基-（9 R，10 S）-环氧庚烷-4,6-diyn-3-one（2）。在光谱证据和不对称合成的基础上阐明了它们的化学结构。获得的IC50值为9 microg / mL（1）和32 microg / mL（2）。
• 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.
• Total synthesis of panaxydol and its stereoisomers as potential anticancer agents
  作者：Jianyou Mao、Shuoning Li、Jiangchun Zhong、Bo Wang、Jing Jin、Zidong Gao、Hanze Yang、Qinghua Bian

  DOI：10.1016/j.tetasy.2015.12.001

  日期：2016.1

  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.
• Studies towards the Biomimetic Synthesis of Ginsenoyne L; Efficient Synthesis of 2'-epi-Ginsenoyne L
  作者：Jack E. Baldwin、Robert M. Adlington、Peter J. Wilkinson、Rodolfo Marquez、Mauro F. A. Adamo

  DOI：10.3987/com-02-s25

  日期：——