(4R)-(2E)-6-methyl-2-hepten-4-ol | 66900-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-(2E)-6-methyl-2-hepten-4-ol
• 英文别名: (R,E)-6-Methyl-3-hepten-4-ol；(R)-rhynchophorol；(r)-6-Methyl-trans-hept-2-en-4-ol；(E,4R)-6-methylhept-2-en-4-ol
• CAS: 66900-48-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: RQAFKZOPSRTJDU-ZJELKQJVSA-N

物化性质

• 沸点：
  162.5±8.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (4R)-(2E)-6-methyl-2-hepten-4-ol 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-2-methyl-4-heptanol 、 (R)-2-methyl-4-heptanol
  参考文献：
  名称：

  Aggregation Pheromones and Host Kairomones of West Indian Sugarcane Weevil, Metamasius hemipterus sericeus

  摘要：

  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.

  DOI：

  10.1023/b:joec.0000006377.13235.4b
• 作为产物：
  描述：

  (+/-)-6-methyl-2-heptyn-4-ol 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (4R)-(2E)-6-methyl-2-hepten-4-ol
  参考文献：
  名称：

  Mori, Kenji; Ishigami, Ken, Liebigs Annalen der Chemie, 1992, # 11, p. 1195 - 1198

  摘要：

  DOI：

文献信息

• Asymmetric Hydrogenation of Alkenyl, Cyclopropyl, and Aryl Ketones. RuCl₂(xylbinap)(1,2-diamine) as a Precatalyst Exhibiting a Wide Scope
  作者：Takeshi Ohkuma、Masatoshi Koizumi、Henri Doucet、Trang Pham、Masami Kozawa、Kunihiko Murata、Eiji Katayama、Tohru Yokozawa、Takao Ikariya、Ryoji Noyori

  DOI：10.1021/ja983257u

  日期：1998.12.1
• Nonshita, Katsumasa; Banno, Hiroshi; Maruoka, Keiji, Journal of the American Chemical Society, 1990, vol. 112, # 1, p. 316 - 322
  作者：Nonshita, Katsumasa、Banno, Hiroshi、Maruoka, Keiji、Yamamoto, Hishashi

  DOI：——

  日期：——
• Hoppe, Dieter; Kraemer, Thomas, Angewandte Chemie, 1986, vol. 98, # 2, p. 171 - 173
  作者：Hoppe, Dieter、Kraemer, Thomas

  DOI：——

  日期：——
• NONOSHITA, KATSUMASA;BANNO, HIROSHI;MARUOKA, KEIJI;YAMAMOTO, HISASHI, J. AMER. CHEM. SOC., 112,(1990) N, C. 316-322
  作者：NONOSHITA, KATSUMASA、BANNO, HIROSHI、MARUOKA, KEIJI、YAMAMOTO, HISASHI

  DOI：——

  日期：——
• 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.