(3S,4S)-3-methyl-4-octanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-3-methyl-4-octanol
• 英文别名: (3S,4S)-3-Methyloctan-4-ol
• 化学式: C₉H₂₀O
• 分子量: 144.257
• InChiKey: MJOKZMZDONULOD-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  5
• 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：

  hept-2-en-1-ol 在 咪唑 、 titanium(IV) isopropylate 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三氟化硼乙醚 、 碘 、 三正丁基氢锡 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 三苯基膦 、 sodium iodide 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 18.16h， 生成 (3S,4S)-3-methyl-4-octanol
  参考文献：
  名称：

  棕榈象鼻小狂犬病菌和菲氏念珠菌以及（+）-反式威士忌内酯的聚集信息素的合成

  摘要：

  （3 S，4 S）-3-甲基辛-4-醇，（4 S，5 S）-4-甲基壬基-5-醇和（+）-反式威士忌内酯[（4 S，5 R）-以自由基环化反应为关键步骤，立体选择性地合成了5-丁基-4-甲基二氢呋喃-2（3 H）-one] 。所有三个分子均由常见的环状缩醛中间体合成。 醇-信息素-内酯-自由基反应-立体选择性合成

  DOI：

  10.1055/s-0031-1289579

文献信息

• <i>α</i>-Sulfenyl-Directed Ring-Opening Reactions of Epoxides. 1. Highly Regio- and Stereoselective Reaction with Organo-Aluminum Reagents and Application to the Synthesis of an Aggregation Pheromone
  作者：Changqing Liu、Yukihiko Hashimoto、Kazuaki Kudo、Kazuhiko Saigo

  DOI：10.1246/bcsj.69.2095

  日期：1996.7

  rearrangement of the sulfenyl group to the C-2 with the complete inversion of the configuration at the C-2. The reactions of these epoxides were considered to proceed via an episulfonium ion intermediate. Upon applying the present reaction, an aggregation pheromone of African Palm Weevil was stereoselectively synthesized in short steps.

  1-苯硫基-2,3-环氧烷烃与三烷基铝的反应显示出明确的 C-2 亲核开环选择性，并得到完全保留 C-2 构型的 C-2 烷基化产物。相比之下，当与烯基（二烷基）铝、二烷基（炔基）铝或 DIBAL 反应时，亲核攻击发生在 C-1 处，伴随着亚磺基重排到 C-2，在C-2。这些环氧化物的反应被认为是通过环锍离子中间体进行的。在应用本反应后，非洲棕榈象鼻虫的聚集信息素在短步骤中立体选择性地合成。
• Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)
  作者：Alice L. Perez、Gerhard Gries、Regine Gries、Robin M. Giblin-Davis、A. Cameron Oehlschlager

  DOI：10.1007/bf02036199

  日期：1994.10

  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.
• Mori, Kenji; Kiyota, Hiromasa; Rochat, Didier, Liebigs Annalen der Chemie, 1993, # 8, p. 865 - 870
  作者：Mori, Kenji、Kiyota, Hiromasa、Rochat, Didier

  DOI：——

  日期：——
• Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.
  作者：José M Odriozola、Jesús M Garcı́a、Alberto González、Pilar Gil

  DOI：10.1016/s0957-4166(99)00528-5

  日期：1999.12

  Syntheses of phoenicol, ferrugineol, and cruentol, aggregation pheromones of Rhynchophorus palm weevils, have been achieved with an overall yield of 42, 40 and 41%, respectively (five steps), in high enantiomeric purity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Syntheses of Aggregation Pheromones of the Palm Weevils Rhyncophorus vulneratus and R. phoenicis and of (+)-trans-Whiskey Lactone
  作者：J. Yadav、C. Rao、A. Prasad、Ahmad Khazim Al Ghamdi

  DOI：10.1055/s-0031-1289579

  日期：2011.12

  (+)-trans-whiskey lactone [(4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one] were synthesized stereoselectively by using a radical cyclization reaction as a key step. All three molecules were synthesized from a common cyclic acetal intermediate. alcohols - pheromones - lactones - radical reactions - stereoselective synthesis

  （3 S，4 S）-3-甲基辛-4-醇，（4 S，5 S）-4-甲基壬基-5-醇和（+）-反式威士忌内酯[（4 S，5 R）-以自由基环化反应为关键步骤，立体选择性地合成了5-丁基-4-甲基二氢呋喃-2（3 H）-one] 。所有三个分子均由常见的环状缩醛中间体合成。 醇-信息素-内酯-自由基反应-立体选择性合成