(R)-2-methyl-4-heptanol | 93031-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-methyl-4-heptanol
• 英文别名: (R)-(-)-2-dodecanol；2-Methylheptan-4R-ol；(4R)-2-methylheptan-4-ol
• CAS: 93031-21-1
• 化学式: C₈H₁₈O
• 分子量: 130.23
• InChiKey: QXPLZEKPCGUWEM-MRVPVSSYSA-N

物化性质

• 沸点：
  164.0±0.0 °C(Predicted)
• 密度：
  0.819±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  L-alpha-羟基异己酸 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 氢溴酸 、 sodium methylate 、 lithium 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 (R)-2-methyl-4-heptanol
  参考文献：
  名称：

  信息素合成，CLXXVII。西印度甘蔗Bor的信息素成分2-甲基-4-庚醇和2-甲基-4-辛醇的对映体的合成†

  摘要：

  由西印度甘蔗synthesized （Metamasius hemipterus）雄性产生的聚集信息素的组分2-甲基-4-庚醇（1）和2-甲基-4-辛醇（2）的对映异构体通过开始合成来自亮氨酸的对映体。

  DOI：

  10.1002/jlac.199619961204

文献信息

• Stereoselective Synthesis of (<i>Z</i>)- and (<i>E</i>)-Allylic Silanes by Copper-Mediated Substitution Reactions of Allylic Carbamates with Grignard Reagents
  作者：Jacqueline H. Smitrovich、K. A. Woerpel

  DOI：10.1021/jo991312r

  日期：2000.3.1

  Both (Z)- and (E)-allylic silanes were prepared with high stereoselectivity by the copper-mediated substitution of allylic carbamates by organometallic reagents. The reaction of alkylmagnesium reagents with (E)-allylic carbamates provides (Z)-allylic silanes, whereas both alkylmagnesium and alkyllithium reagents react with (Z)-allylic carbamates to afford (E)-allylic silanes. Because Grignard reagents

  （Z）-和（E）-烯丙基硅烷都通过有机金属试剂通过铜介导的烯丙基氨基甲酸酯的铜取代而以高立体选择性制备。烷基镁试剂与（E）-烯丙基氨基甲酸酯的反应提供（Z）-烯丙基硅烷，而烷基镁和烷基锂试剂都与（Z）-烯丙基氨基甲酸酯反应以提供（E）-烯丙基硅烷。由于格氏试剂通常比烷基锂种类更易于制备，因此这些试剂是合成（Z）-和（E）-烯丙基硅烷的最佳亲核试剂。该方法还允许容易获得的非外消旋烯丙基氨基甲酸酯以高的立体选择性转化为手性，非外消旋（Z）-和（E）-烯丙基硅烷。
• On the Stereochemical Course of Palladium-Catalyzed Cross-Coupling of Allylic Silanolate Salts with Aromatic Bromides
  作者：Scott E. Denmark、Nathan S. Werner

  DOI：10.1021/ja910804u

  日期：2010.3.17

  palladium-catalyzed cross-coupling reactions of an enantioenriched, alpha-substituted, allylic silanolate salt with aromatic bromides has been investigated. The allylic silanolate salt was prepared in high geometrical (Z/E, 94:6) and high enantiomeric (94:6 er) purity by a copper-catalyzed S(N)2' reaction of a resolved allylic carbamate. Eight different aromatic bromides underwent cross-coupling with excellent

  已经研究了钯催化的对映体富集的、α 取代的烯丙基硅烷醇盐与芳族溴化物的交叉偶联反应的立体化学过程。通过铜催化的 S(N)2' 反应分解的烯丙基氨基甲酸酯，以高几何 (Z/E，94:6) 和高对映体 (94:6 er) 纯度制备烯丙基硅烷醇盐。八种不同的芳香族溴化物以优异的结构位点选择性和立体特异性进行交叉偶联。立体化学相关性确定金属转移事件通过 Syn S(E)' 机制进行，该机制解释为芳基钯亲电试剂通过包含离散 Si-O-Pd 键的关键中间体的分子内传递。
• Efficient synthesis of (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol: the pheromones of Myrmica scabrinodis, Crematogaster castanea, C. liengmei, C. auberti and Metamasius hemipterus
  作者：Byung Tae Cho、Dong Jun Kim

  DOI：10.1016/s0040-4020(03)00254-0

  日期：2003.3

  A simple and efficient synthesis of optically active insect pheromones, such as (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol starting from non-racemic β-hydroxy sulfides has been established.

  简单有效地合成旋光昆虫信息素，例如（R）-和（S）-3-辛醇，（R）-2-十二烷醇，（R）-2-甲基-4-庚醇和（R）-已经建立了从非外消旋β-羟基硫化物开始的2-甲基-4-辛醇。
• PYRAZOLOPYRIMIDINE JAK INHIBITOR COMPOUNDS AND METHODS
  申请人：Gibbons Paul

  公开号：US20120190665A1

  公开（公告）日：2012-07-26

  A compound of Formula I, enantiomers, diasteriomers, tautomers or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 and R 3 are defined herein, are useful as inhibitors of one or more Janus kinases. A pharmaceutical composition that includes a compound of Formula I and a pharmaceutically acceptable carrier, adjuvant or vehicle, and methods of treating or lessening the severity of a disease or condition responsive to the inhibition of a Janus kinase activity in a patient are disclosed.

  公式I的化合物、对映异构体、顺反异构体、互变异构体或其药学上可接受的盐，其中R1、R2和R3的定义如本文所述，可用作一种或多种Janus激酶的抑制剂。本文还揭示了一种包括公式I的化合物和药学上可接受的载体、辅料或载体的药物组合物，以及治疗或减轻患者对Janus激酶活性抑制响应的疾病或状况的方法。
• Aggregation Pheromones and Host Kairomones of West Indian Sugarcane Weevil, Metamasius hemipterus sericeus
  作者：A. L. Perez、Y. Campos、C. M. Chinchilla、A. C. Oehlschlager、G. Gries、R. Gries、R. M. Giblin-Davis、G. Castrillo、J. E. Peña、R. E. Duncan、L. M. Gonzalez、H. D. Pierce, Jr.、R. McDonald、R. Andrade

  DOI：10.1023/b:joec.0000006377.13235.4b

  日期：1997.4

  Coupled gas chromatagraphic-electroantennographic detection (GC-EAD) analyses and coupled CC-mass spectrometry (MS) of volatiles produced by male and female West Indian sugarcane weevils (WISW), Metamasius hemipterus sericeus (Oliv.), revealed eight male specific, EAD-active compounds: 3-pentanol (1), 2-methyl-4-heptanol (2), 2-methyl-4-octanol (3), 4-methyl-5-nonanol (4), and the corresponding ketones. In field experiments in Florida, alcohols 1-4 in combination with sugarcane were most attractive, whereas addition of the ketones or replacement of alcohols with ketones significantly reduced attraction. In Costa Rica field experiments testing alcohols 1-4 singly and in all binary, ternary, and quaternary combinations revealed 4 in combination with 2 was the major aggregation pheromone, equally attracting male and female WISW. Stereoisomeric 4 and (4S,5S)-4, the only isomer produced by WISW, were equally attractive. Addition of 4S-, 4R- or (+/-)-2 to (4S,5S)-4 significantly enhanced attraction. Sugarcane stalks in combination with 2 plus 4 (ratio of 1:8) were highly synergistic, whereas EAD-active sugarcane volatiles ethyl acetate, ethyl propionate, or ethyl butyrate only moderately increased attractiveness of the pheromone lure.