(-)-(R)-10-methyldodecyl acetate | 71777-34-9

• 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: (-)-(R)-10-methyldodecyl acetate
• 英文别名: (r)-10-Methyldodecyl acetate；[(10R)-10-methyldodecyl] acetate
• CAS: 71777-34-9
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: WUVOJIMYHUYERX-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 萘 、 lithium 作用下， 以 溶剂黄146 为溶剂， 反应 1.08h， 生成 (-)-(R)-10-methyldodecyl acetate
  参考文献：
  名称：

  Stereospecific dehydrative alkylation of bis-sulfones: synthesis of a lesser tea tortrix pheromone

  摘要：

  The intra- and intermolecular condensation of alcohols with bis-sulfone methylenes, i.e., dehydrative alkylation, using DEAD and Ph3P proceeds stereospecifically at room temperature under essentially neutral conditions affording good to excellent yields of alkylation/annulation products.

  DOI：

  10.1021/jo00074a010

文献信息

• Hydrolytic kinetic resolution of terminal mono- and bis-epoxides in the synthesis of insect pheromones: routes to (−)-( R )- and (+)-( S )-10-methyldodecyl acetate, (−)-( R )-10-methyl-2-tridecanone, (−)-( R )-( Z )-undec-6-en-2-ol (Nostrenol), (−)-(1 R ,7 R )-1,7-dimethylnonyl propanoate, (−)-(6 R ,12 R )-6,12-dimethylpentadecan-2-one, (−)-(2 S ,11 S )-2,11-diacetoxytridecane and (+)-(2 S ,12 S )-2,12-diacetoxytridecane
  作者：Sharon Chow、William Kitching

  DOI：10.1016/s0957-4166(02)00175-1

  日期：2002.5

  enantiomerically enriched epoxides and diols, which have been transformed into important insect sex pheromones. In this general approach, (−)-(R)- and (+)-(S)-10-methyldodecyl acetates from the smaller tea tortrix moth were obtained, as was (−)-(R)-10-methyltridecan-2-one from the southern corn rootworm. The (S)-epoxide obtained from undec-1-en-6-yne was transformed to (−)-(R)-(Z)-undec-6-en-2-ol (Nostrenol)

  使用（salen）Co（OAc）配合物的官能化环氧化物的水解动力学拆分（HKR）提供了对映体富集的环氧化物和二醇，它们已转化为重要的昆虫性信息素。在这种通用方法中，从较小的茶to蛾中获得了（-）-（R）-和（+）-（S）-10-甲基十二烷基乙酸酯，以及（-）-（R）-10-甲基叔丁基酚2 -来自南部玉米根虫的一种。从十一烯-1-烯-6-炔获得的（S）-环氧化物从蚁狮转变为（-）-（R）-（Z）-十一烯-6-烯-2-醇（Nostrenol）。还研究了合适的双环氧化物的HKR，并提供了生成的双环氧化物和环氧二醇的转化（-）-（1 R，7 - [R ）从玉米根-1,7- dimethylnonylpropanoate，（ - ） - （6 - [R，12 - [R）-6,12-dimethylpentadecan -2-酮从阴带状黄瓜甲虫，和（ - ） - （2-小号来自雌豌豆mid的，11 S
• Hydrolytic kinetic resolution of mono- and bisepoxides as a key step in the synthesis of insect pheromones
  作者：Sharon Chow、William Kitching

  DOI：10.1039/b102181h

  日期：——

  The synthetic utility of the readily separated epoxides, diols, epoxydiols and tetrols of high enantiomeric excesses, obtained by hydrolytic kinetic resolution (HKR) of functionalised mono- and bisepoxides with (salen)Co(OAc) complexes, is demonstrated by their efficient transformations to important insect pheromones.

  通过使用 (salen)Co(OAc) complexes 对功能化的单环和双环环氧化物进行水解动力学分辨 (HKR) 所获得的高对映体过量的易分离环氧化物、二醇、环氧二醇和四醇的合成实用性，通过其高效转化为重要的昆虫信息素得以体现。
• Preparation of the versatile chiron, (R)- and (S)-12-(tetrahydropyranyloxy)-3-methyldodecan-1-ol: application to the syntheses of methyl branched insect pheromones
  作者：S. Sankaranarayanan、A. Sharma、B. A. Kulkarni、S. Chattopadhyay

  DOI：10.1021/jo00118a047

  日期：1995.6

  A convenient chemoenzymatic synthesis for the title methyl branched chiron has been developed starting from 10-undecenoic acid (1). Thus, 1 was converted to 1-(tetrahydropyranyloxy)-10-undecan-2-one (4) which on reaction with triethyl phosphonoacetate and subsequent functionalization led to the racemic chiron 7. This was resolved via C. rugosa lipase-catalyzed acetylation and subsequently used for the syntheses of some chiral insect pheromones. Thus, (S)-7 was mesylated, reduced with LAH and acetylated to give the pheromone (R)-10-methyldodecan-1-yl acetate (I), while its oxidation to the aldehyde 10 followed by Wittig reaction with methylenephosphorane, depyranylation, and hydrogenation gave the alcohol 12. Its tosylation, detosylation, and Hg2+-catalyzed hydration furnished (R)-10-methyltridecan-2-one (II). Likewise, Wittig reaction of (R)-10 with a suitable phosphorane and similar protocol as above afforded the alcohol 14. Its tosylate was coupled with 3-butenylmagnesium bromide to furnish pheromone (S)-14-methyloctadecene (III).
• Chiral synthesis via organoboranes. 12. Conversion of boronic esters of essentially 100% optical purity into monoalkylthexylboranes providing convenient synthetic routes to trans-olefins, cis-olefins, alkynes, and ketones of very high enantiomeric purities
  作者：Herbert C. Brown、Raman K. Bakshi、Bakthan. Singaram

  DOI：10.1021/ja00213a028

  日期：1988.3
• Hjalmarsson, Mats; Hoegberg, Hans-Erik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 9, p. 793 - 796
  作者：Hjalmarsson, Mats、Hoegberg, Hans-Erik

  DOI：——

  日期：——