(3R,4R,5S)-3,5-Dimethyl-1-hepten-4-ol | 82917-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S)-3,5-Dimethyl-1-hepten-4-ol
• 英文别名: (3R,4R,5S)-3,5-dimethylhept-1-en-4-ol
• CAS: 82917-17-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: MVTVDAPLCOTIFV-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (3R,4R,5S)-3,5-Dimethyl-1-hepten-4-ol 在 platinum on activated charcoal 氢气 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 生成 (3R*,4R*,5S*)-3,5-dimethylheptan-4-ol
  参考文献：
  名称：

  Hoffmann, Reinhard W.; Zeiss, Hans-Joachim; Ladner, Wolfgang, Chemische Berichte, 1982, vol. 115, # 6, p. 2357 - 2370

  摘要：

  DOI：
• 作为产物：
  描述：

  S-(-)-2-甲基-1-丁醇 在 sodium hydroxide 、 sodium dichromate 、 硫酸 、 双氧水 作用下， 以 水 为溶剂， 反应 4.75h， 生成 (3R,4R,5S)-3,5-Dimethyl-1-hepten-4-ol
  参考文献：
  名称：

  A convergent synthesis of the C(11)–C(25) fragment of the aglycone of avermectin A2b

  摘要：

  Oxidation of the mixture of products obtained by treatment of (S)-2-methylbutanal 8 with the E-but-2-enyldi-isopinocampheylborane prepared from (+)-pinene gave a mixture of homoallylic alcohols from which the major isomer 9 was isolated by chromatography. Oxidation with vanadylacetoacetate and tert-butyl hydroperoxide gave the epoxides 12 and 13, ratio 80 : 20. Following procedures developed in a synthesis of the model spiroacetal 19, 1,3-dithiane was alkylated, firstly using the epoxide 12, and then, after protection of the product 21 so obtained as its acetonide 23, using the epoxide 25, to give the 2,2-dialkylated 1,3-dithiane 25. Deprotection was accompanied by cyclisation to give the spiroacetal 28. Spiroacetal 29 was similarly prepared and taken through to the C(11)-C(25) fragment 38 of the aglycone of avermectin A(2b) 3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00590-5

文献信息

• Total Synthesis of the Antiparasitic Agent Avermectin B1a
  作者：James D. White、Gary L. Bolton、Anura P. Dantanarayana、Christina M. J. Fox、Roger N. Hiner、Randy W. Jackson、Kazuhiko Sakuma、Ulhas S. Warrier

  DOI：10.1021/ja00112a006

  日期：1995.2

  The synthesis of avermectin B-1a has been completed by a route that assembles the aglycon from three subunits consisting of the hexahydrobenzofuran moiety (A), the spiroketal segment (B), and the acyclic portion (C) comprising C9-C15. Connection is made in a B + C --> (B - C) + A sequence, and the synthesis is concluded by attachment to the aglycon of the L-oleandrosyl-L-oleandrose disaccharide via the pyridylthio glycoside.
• Chiral synthesis via organoboranes. 21. Allyl- and crotylboration of .alpha.-chiral aldehydes with diisopinocampheylboron as the chiral auxiliary
  作者：Herbert C. Brown、Krishna S. Bhat、Ramnarayan S. Randad

  DOI：10.1021/jo00268a017

  日期：1989.3
• Hoffmann, Reinhard W.; Zeiss, Hans-Joachim, Angewandte Chemie, 1980, vol. 92, # 3, p. 218 - 223
  作者：Hoffmann, Reinhard W.、Zeiss, Hans-Joachim

  DOI：——

  日期：——
• BROWN, HERBERT C.;BHAT, KRISHNA S.;RANDAD, RAMNARAYAN S., J. ORG. CHEM., 54,(1989) N, C. 1570-1576
  作者：BROWN, HERBERT C.、BHAT, KRISHNA S.、RANDAD, RAMNARAYAN S.

  DOI：——

  日期：——
• BRINKMANN, HEINRICH;, HOFFMANN REINHARD W., CHEM. BER., 123,(1990) N2, C. 2395-2401
  作者：BRINKMANN, HEINRICH、, HOFFMANN REINHARD W.

  DOI：——

  日期：——