(R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol | 546084-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol
• 英文别名: (3R)-5-trimethylsilyl-1-penten-4-yn-3-ol；(R)-5-trimethylsilyl-1-penten-4-yn-3-ol；5-(trimethylsilyl)pent-1-en-4-yn-3-ol；(3R)-5-trimethylsilylpent-1-en-4-yn-3-ol
• CAS: 546084-18-8
• 化学式: C₈H₁₄OSi
• 分子量: 154.284
• InChiKey: FZXPLTZXRLCCRC-MRVPVSSYSA-N

物化性质

• 沸点：
  189.5±28.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 反应 1.0h， 以136 mg的产率得到(R)-5-bromo-1-penten-4-yn-3-ol
  参考文献：
  名称：

  Alkynol natural products target ALDH2 in cancer cells by irreversible binding to the active site

  摘要：

  化学蛋白质组学研究揭示了ALDH2在癌细胞中作为falcarinol的分子靶点。

  DOI：

  10.1039/c5cc06424d
• 作为产物：
  描述：

  5-trimethylsilyl-1-penten-4-yn-3-one 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol
  参考文献：
  名称：

  Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.01.047

文献信息

• Highly Enantioselective Addition of Trimethylsilylacetylene to Aldehydes Catalyzed by a Zinc-Amino-Alcohol Complex
  作者：Zhi-Yuan Li、Min Wang、Qing-Hua Bian、Bing Zheng、Jian-You Mao、Shuo-Ning Li、Shang-Zhong Liu、Ming-An Wang、Jiang-Chun Zhong、Hong-Chao Guo

  DOI：10.1002/chem.201100535

  日期：2011.5.16

  A fine addition! A highly enantioselective and efficient procedure for the amino‐alcohol–zinc‐catalyzed addition of trimethylsilylacetylene to aromatic, α,β‐unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS=tert‐butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine

  很好的补充！已开发出一种高度对映选择性和高效的程序，用于氨基醇锌催化的三甲基甲硅烷基乙炔加成到芳族，α，β-不饱和和脂肪族醛中（见方案； R =芳基，炔基或烷基； TMS =三甲基甲硅烷基； TBDMS =叔丁基二甲基甲硅烷基）。本协议已成功地应用于天然产物海洋炔醇和法卡林二醇的简明合成中。
• COMPOUNDS, COMPOSITIONS AND METHODS FOR REDUCING TOXICITY AND TREATING OR PREVENTING DISEASES
  申请人：Danishefsky Samuel J.

  公开号：US20110312904A1

  公开（公告）日：2011-12-22

  The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).

  本发明提供了公式(I)的化合物，以及包含公式(I)化合物的有效量的组合物，可选地与化疗药物如微管结合药物一起使用，并用于减少细胞毒性药物的毒性，治疗或预防癌症或神经病理性障碍，诱导化学保护性II期酶、DNA或蛋白质合成，增强免疫系统，治疗炎症，改善和增强整体健康或福祉，以及制备公式(I)化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING CANCER OR A NEUROTROPHIC DISORDER
  申请人：Danishefsky Samuel J.

  公开号：US20110124690A1

  公开（公告）日：2011-05-26

  The present invention relates to compositions comprising an effective amount of a Panaxytriol Compound and a tubulin-binding drug, methods for treating or preventing cancer or a neurotrophic disorder comprising administering to a subject in need thereof an effective amount of a Panaxytriol Compound and a tubulin-binding drug, and methods for making a Panaxytriol Compound.

  本发明涉及组合物，包括有效量的泛沙三醇化合物和微管结合药物，治疗或预防癌症或神经营养障碍的方法包括向需要的受体中投与有效量的泛沙三醇化合物和微管结合药物，以及制备泛沙三醇化合物的方法。
• Compounds, compositions and methods for reducing toxicity and treating or preventing diseases
  申请人：Danishefsky Samuel J.

  公开号：US08859615B2

  公开（公告）日：2014-10-14

  The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).

  本发明提供公式（I）化合物，包括含有公式（I）化合物的有效量的组合物，可选地与化疗药物如微管结合药物一起使用，并用于降低细胞毒性药剂的毒性，治疗或预防癌症或神经病理性疾病，诱导化学保护期II酶、DNA或蛋白质的合成，增强免疫系统，治疗炎症，改善和增强一般健康或福祉，并提供公式（I）化合物的制备方法。
• 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.