3(R)-(t-butyldiphenylsilyloxy)-1-penten-4-yne | 224636-36-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3(R)-(t-butyldiphenylsilyloxy)-1-penten-4-yne
• 英文别名: (3R)-tert-butyldiphenylsilyloxy-pent-1-en-4-yne；3(R)-(tert-butyldiphenylsilyloxy)-1-penten-4-yne；(3R)-(t-butyldiphenylsilyloxy)-pent-1-en-4-yne；tert-butyl-[(3R)-pent-1-en-4-yn-3-yl]oxy-diphenylsilane
• CAS: 224636-36-6
• 化学式: C₂₁H₂₄OSi
• 分子量: 320.506
• InChiKey: UIHHFMRPBOACDZ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3(R)-(t-butyldiphenylsilyloxy)-1-penten-4-yne 在 盐酸羟胺 、 四丁基氟化铵 、 乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.17h， 生成 人参炔三醇
  参考文献：
  名称：

  Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from panax ginseng

  摘要：

  (3R, 9R, 10R) 和 (3R, 9S, 10S) 对映异构体 (2 和 3) 的PA3（panaxytriol）通过合成得到了，并确认了PA3的绝对构型为(3R, 9R, 10R)-heptadec-1-en-4,6-diyne-3,9,10-triol。 © 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4020(99)00352-x
• 作为产物：
  描述：

  (3R)-1,1-dibromo-3-tert-butyldiphenylsilyloxy-1,4-pentdiene 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到3(R)-(t-butyldiphenylsilyloxy)-1-penten-4-yne
  参考文献：
  名称：

  Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from panax ginseng

  摘要：

  (3R, 9R, 10R) 和 (3R, 9S, 10S) 对映异构体 (2 和 3) 的PA3（panaxytriol）通过合成得到了，并确认了PA3的绝对构型为(3R, 9R, 10R)-heptadec-1-en-4,6-diyne-3,9,10-triol。 © 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4020(99)00352-x

文献信息

• Stereoselective Synthesis of (3<i>S</i>,8<i>R</i>,9<i>R</i>,10<i>R</i>)-Heptadeca-1-ene-4,6-diyne Tetrol and Its 3-Epimer from <scp>d</scp>-Mannitol
  作者：Subhash Ghosh、Tapan Pradhan

  DOI：10.1055/s-2007-985598

  日期：2007.9

  (3S,8R,9R,10R)-Heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer were synthesized, and it was found that the relative configuration which was proposed for 1 was incorrect.

  合成了（3S,8R,9R,10R）-十七碳-1-烯-4,6-二炔四醇及其3-表异构体，并发现先前为1提出的相对构型是不正确的。
• First total synthesis of optically active panaxydol, a potential antitumor agent isolated from Panax ginseng
  作者：Wei Lu、Guangrong Zheng、Haji、A. Aisa、Junchao Cai

  DOI：10.1016/s0040-4039(98)02212-6

  日期：1998.12

  The first total synthesis of panaxydol 1 is described, starting from L-(+)-diethyl tartrate 2.

  从L-（+）-酒石酸二乙酯2开始，描述了人参醇1的第一个全合成。
• Stereoselective Total Synthesis of (3<i>R</i>,8<i>S</i>)-Falcarindiol, a Common Polyacetylenic Compound from Umbellifers
  作者：Guangrong Zheng、Wei Lu、Junchao Cai

  DOI：10.1021/np980418z

  日期：1999.4.1

  The first stereoselective total synthesis of (3R,8S)-falcarindiol (1) from L-tartaric acid and D-xylose is reported, via the Cadiot-Chodkiczwicz reaction, to couple 1-bromoalkyne (2) with 3(R)-(tert-butyldiphenylsilyloxy)-1-penten-4-yne (3).

  据报道，通过Cadiot-Chodkiczwicz反应，由L-酒石酸和D-木糖首次立体选择性地合成（3R，8S）-法卡林二醇（1），将1-溴代炔烃（2）与3（R）-（叔丁基二苯基甲硅烷氧基）-1-戊烯-4-炔（3）。
• Ivorenolide B, an Immunosuppressive 17-Membered Macrolide from <i>Khaya ivorensis</i>: Structural Determination and Total Synthesis
  作者：Yao Wang、Qun-Fang Liu、Ji-Jun Xue、Yu Zhou、Huang-Chao Yu、Sheng-Ping Yang、Bo Zhang、Jian-Ping Zuo、Ying Li、Jian-Min Yue

  DOI：10.1021/ol500667d

  日期：2014.4.4

  Ivorenolide B (1), an unprecedented 17-membered macrolide featuring conjugated acetylenic bonds and four chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis and total syntheses of its four most possible stereoisomers. Compound 1 showed significant immunosuppressive activity.

  Ivorenolide B（1）是一种空前的17元大环内酯，具有共轭炔键和四个手性中心，是从Khaya ivorensis中分离出来的。1的结构通过光谱分析及其四种最可能的立体异构体的总合成来完全确定。化合物1显示出明显的免疫抑制活性。
• Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma
  作者：Satoru Tamura、Tomomichi Ohno、Yuuhi Hattori、Nobutoshi Murakami

  DOI：10.1016/j.tetlet.2010.01.047

  日期：2010.3

  Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this active principle, all three stereoisomers as well as falcarindiol (1) were synthesized. As a result of intensive analysis of their physicochemical properties, the configuration of I was revealed to be 3R,8S. On the other hand, (3S,8S)- and (3S,8R)-isomers were found to exhibit more potent algicidal activity than (3R,8S)-falcarindiol (1) isolated from Notopterygii Rhizoma. In addition, the diyne moiety of 1 was established as the crucial structural requirement for algicidal potency. (C) 2010 Elsevier Ltd. All rights reserved.