(3S)-3-methyldecan-1-ol

• 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: (3S)-3-methyldecan-1-ol
• 英文别名: 3(S)-methyldecan-1-ol
• 化学式: C₁₁H₂₄O
• 分子量: 172.311
• InChiKey: IMACNEKKOHOIMA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  8
• 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：

  (3S)-3-methyldecan-1-ol 在 吡啶 、 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (4S)-4-methylundecan-1-ol
  参考文献：
  名称：

  (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one as an efficient intermediate in the preparation of chiral building blocks with methyl-branched carbon skeleton. Application to the synthesis of bioactive compounds

  摘要：

  Synthesis was performed of (3S)-3-methyldecen-1-ol and (4S)-4-methylundecen-1-ol, chiral alcohols with a methyl-branched carbon skeleton. The possibility of their application in asymmetric syntheses of insect pheromones was demonstrated.

  DOI：

  10.1134/s1070428014110141
• 作为产物：
  描述：

  (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one 在 咪唑 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 (3S)-3-methyldecan-1-ol
  参考文献：
  名称：

  (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one as an efficient intermediate in the preparation of chiral building blocks with methyl-branched carbon skeleton. Application to the synthesis of bioactive compounds

  摘要：

  Synthesis was performed of (3S)-3-methyldecen-1-ol and (4S)-4-methylundecen-1-ol, chiral alcohols with a methyl-branched carbon skeleton. The possibility of their application in asymmetric syntheses of insect pheromones was demonstrated.

  DOI：

  10.1134/s1070428014110141

文献信息

• Highly Selective Synthesis of (<i>E</i>)-3-Methyl-1-trialkylsilyl-3-en-1-ynes via <i>trans</i>-Selective Alkynylation Catalyzed by Cl₂Pd(DPEphos) and Stereospecific Methylation with Methylzincs Catalyzed by Pd(<i>^t</i>Bu₃P)₂
  作者：Ji-cheng Shi、Xingzhong Zeng、Ei-ichi Negishi

  DOI：10.1021/ol030017x

  日期：2003.5.1

  [reaction: see text] trans-Selective (>or=98%) monoalkynylation of 1,1-dibromo-1-alkenes and 1,1-dichloro-1-alkenes catalyzed by Cl(2)Pd(DPEphos) followed by stereospecific methylation with Me(2)Zn or MeZnX (X= Cl or Br) catalyzed by Pd((t)()Bu(3)P)(2) provides an efficient and stereoselective (>or=98%) route to 5, convertible to a wide variety of enynes and conjugated dienes. In the cases of 1,1-dibromo-1-alkenes

  [反应：见正文]由Cl（2）Pd（DPEphos）催化的立体选择性催化的1,1-二溴-1-烯烃和1,1-二氯-1-烯烃的反式选择性（>或= 98％）单烷基化由Pd（（t）（）Bu（3）P）（2）催化的Me（2）Zn或MeZnX（X = Cl或Br）甲基化可提供有效且立体选择性的途径（>或= 98％）生成5，可转换为多种烯炔和共轭二烯。在1，1-二溴-1-链烯的情况下，Sonogashira炔基化也可能是令人满意的，但是在使用1，1-二氯-1-链烯的情况下，它明显不如炔基锌反应令人满意。
• 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。
• 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
• (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one as an efficient intermediate in the preparation of chiral building blocks with methyl-branched carbon skeleton. Application to the synthesis of bioactive compounds
  作者：I. V. Mineyeva、V. S. Masyuk、V. N. Kovalenko、M. M. Bandarenko

  DOI：10.1134/s1070428014110141

  日期：2014.11

  Synthesis was performed of (3S)-3-methyldecen-1-ol and (4S)-4-methylundecen-1-ol, chiral alcohols with a methyl-branched carbon skeleton. The possibility of their application in asymmetric syntheses of insect pheromones was demonstrated.