(2R,3R)-3-Methyl-hexane-1,2-diol | 94992-81-1

• 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: (2R,3R)-3-Methyl-hexane-1,2-diol
• 英文别名: (2R,3R)-3-methylhexane-1,2-diol
• CAS: 94992-81-1
• 化学式: C₇H₁₆O₂
• 分子量: 132.203
• InChiKey: MSCWGJFHWUZSAO-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Methyl-hexane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醚 为溶剂， 反应 7.5h， 生成 (S,R)-Cruentol
  参考文献：
  名称：

  Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

  摘要：

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

  DOI：

  10.1007/bf02036199
• 作为产物：
  描述：

  (E)-3-Methylhex-2-en-1-ol THP-ether 生成 (2R,3R)-3-Methyl-hexane-1,2-diol
  参考文献：
  名称：

  （−）-4-methylheptan-3-ol（欧洲小榆树皮甲虫的信息素）的绝对构型，由其（3 R，4 R）-（+）-和（3 S，4的合成确定R）-（+）-异构体

  摘要：

  将Nerol和香叶醇分别立体选择性地转化为（±）-苏式-和（±）-赤型-4-甲基庚烷-3-醇。将（R）-（+）-香acid酸转化为（3 R，4 R）-（+）-苏式-和（3 S，4 R）-（+）-赤型异构体的混合物GLC。这些合成建立的天然存在的绝对构型（ - ） - 4-甲基庚-3-醇为3小号，4小号。

  DOI：

  10.1016/0040-4020(77)80108-7

文献信息

• The C2 Selective Nucleophilic Substitution Reactions of 2,3-Epoxy Alcohols Mediated by Trialkyl Borates:  The First <i>endo</i>-Mode Epoxide-Opening Reaction through an Intramolecular Metal Chelate
  作者：Minoru Sasaki、Keiji Tanino、Atsushi Hirai、Masaaki Miyashita

  DOI：10.1021/ol034455f

  日期：2003.5.1

  [reaction: see text] Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN(3)-(CH(3)O)(3)B, NaSPh-(CH(3)O)(3)B, or NaCN-(C(2)H(5)O)(3)B system. The reaction proceeds through novel endo-mode epoxide opening of an intramolecular boron chelate, which was suggested from both experimental and quantum mechanic studies.

  [反应：参见文本]通过使用NaN（3）-（CH（3）O）（3）B，NaSPh-（CH（3）O）开发了2,3-环氧醇与亲核试剂的高效C2选择取代反应）（3）B或NaCN-（C（2）H（5）O）（3）B系统。该反应通过分子内硼螯合物的新型内模环氧化物开口而进行，这是从实验和量子力学研究中提出的。
• Determination of absolute configurations of β- or γ-methyl substituted secondary alcohols by NMR spectroscopy
  作者：Haruko Takahashi、Makoto Iwashima、Kazuo Iguchi

  DOI：10.1016/s0040-4039(98)02344-2

  日期：1999.1

  determining the absolute configurations of acyclic β- or γ-methyl substituted secondary alcohols using their 2NMA esters. The 1H-NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δR-ester - δS-ester) for the corresponding protons were compared between syn and anti compounds. Threshold values important for judging the relative stereochemistry of the two chiral centers

  已经开发出一种新方法，用于使用2NMA酯测定无环β-或γ-甲基取代的仲醇的绝对构型。的1的H-NMR谱（[R ）-和（小号）测量模型化合物的-2NMA酯和Δδ值（δ R-酯- δ S-酯），用于相应的质子之间比较顺式和反化合物。获得了对于判断两个带有甲基和羟基的手性中心的相对立体化学重要的阈值。如MTPA方法那样，容易基于Δδ值的符号来确定带有仲羟基的手性中心的绝对构型，因此在本研究中，也可以清楚地确定带有甲基的手性中心的绝对构型。团体。
• Total Synthesis of the Reported Structure of Neaumycin B
  作者：Jiaming Ding、Amos B. Smith

  DOI：10.1021/jacs.3c06573

  日期：2023.8.23

  stereoselective total synthesis of structure 1 assigned to the macrolide natural product neaumycin B is reported in a 2.3% overall yield on 90 mg scale. The synthesis features a gram-scale nickel-catalyzed reductive cross-coupling/spiroketalization tactic to construct the spiroketal core of neaumycin B. The stereostructures of the C3–C6, C8–C14, and C20–C41 segments of synthetic neaumycin B were unambiguously

  据报道，大环内酯天然产物新霉素 B 的结构1的立体选择性全合成在 90 mg 规模上的总产率为 2.3%。该合成采用克级镍催化还原交叉偶联/螺酮化策略来构建新霉素 B 的螺酮核心。合成新霉素 B 的 C3–C6、C8–C14 和 C20–C41 片段的立体结构得到了明确验证。通过X射线晶体学。
• Total synthesis of the unusual cyclosporine amino acid MeBMT
  作者：Roger D Tung、Daniel H Rich

  DOI：10.1016/s0040-4039(00)95309-7

  日期：1987.1
• OPPOLZER, W.;DUDFIELD, P., HELV. CHIM. ACTA, 1985, 68, N 1, 216-219
  作者：OPPOLZER, W.、DUDFIELD, P.

  DOI：——

  日期：——