4(S),8-dimethylnonan-1-ol | 87187-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4(S),8-dimethylnonan-1-ol
• 英文别名: (4S)-4,8-dimethylnonan-1-ol
• CAS: 87187-92-6
• 化学式: C₁₁H₂₄O
• 分子量: 172.311
• InChiKey: ASDSWUHLJCTXPE-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  4(S),8-dimethylnonan-1-ol 在 亚磷酸三苯酯 、 草酰氯 、 溴 、 potassium hydride 、 二甲基亚砜 、 1,3-丙二胺 、 三乙胺 作用下， 以 二氯甲烷 、 mineral oil 为溶剂， 反应 5.5h， 生成 (4S)-4,8-dimethylnon-1-yne
  参考文献：
  名称：

  Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling

  摘要：

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.019
• 作为产物：
  描述：

  (R)-甲基-5-溴-4-甲基戊酸酯 在 lithium aluminium tetrahydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 4(S),8-dimethylnonan-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling

  摘要：

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.019

文献信息

• Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton-Part 2
  作者：Ko Yasumoto、Akinori Nishigami、Hiroaki Aoi、Chise Tsuchihashi、Fumie Kasai、Takenori Kusumi、Takashi Ooi

  DOI：10.1248/cpb.56.129

  日期：——

  4,8-Dimethylnonyl sulfate (1) and 3-methyl-4E-decenyl sulfate (2) were isolated from Daphnia pulex as the Daphnia kairomones that induced morphological defense of a freshwater phytoplankton Scenedesmus gutwinskii var. heterospina (NIES-802). The absolute configuration at C4 of 1 was determined by Ohrui's method applied to alcohol 3. The absolute stereochemistry at C3 of 2 was determined by 1H-NMR analysis of the (R)-1NMA ester of alcohol 11.

  4,8-二甲基壬基硫酸酯（1）和3-甲基-4E-癸烯基硫酸酯（2）是从水蚤Daphnia pulex中分离得到的两种信息素，能够诱导淡水浮游植物Scenedesmus gutwinskii var. heterospina（NIES-802）产生形态防御反应。根据Ohrui的方法对醇3的应用，确定了化合物1在C4位的绝对构型。通过分析醇11的（R）-1NMA酯的1H-NMR，确定了化合物2在C3位的绝对立体化学。
• Enantioselective hydrogenation of allylic and homoallylic alcohols
  作者：Hidemasa Takaya、Tetsuo Ohta、Noboru Sayo、Hidenori Kumobayashi、Susumu Akutagawa、Shinichi Inoue、Isamu Kasahara、Ryoji Noyori

  DOI：10.1021/ja00239a065

  日期：1987.3

  Hydrogenation enantioselective en particulier du geraniol et du nerol catalysee par des complexes dicarboxylato du ruthenium(II) contenant des coordinats bis-diarylphosphino-2,2' binaphtyles-1,1'

  氢化对映选择性en particulier du geraniol et du nerol catalysee par des complexes dicarboxylato du ruthenium(II) contenant des coordinats bis-diarylphosphino-2,2' binaphtyles-1,1'
• A New Protocol for the Enantioselective Synthesis of Methyl-Substituted Alkanols and Their Derivatives through a Hydroalumination/Zirconium-Catalyzed Alkylalumination Tandem Process We thank the National Science Foundation (CHE-0080795), the National Institutes of Health (GM36792), and Purdue University for support of this research. We also thank Albemarle and Boulder Chemical for assistance in the procurement of Al and Zr compounds, respectively.
  作者：Shouquan Huo、Ji-cheng Shi、Ei-ichi Negishi

  DOI：10.1002/1521-3773(20020617)41:12<2141::aid-anie2141>3.0.co;2-w

  日期：2002.6.17
• Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling
  作者：Shunji Zhang、Huaide Dong、Jinghan Gui、Weisheng Tian

  DOI：10.1016/j.tetlet.2012.02.019

  日期：2012.4

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.