(Z)-5,5-dimethylhex-3-en-2-ol | 2747-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5,5-dimethylhex-3-en-2-ol
• 英文别名: cis-2,2-Dimethyl-hexen-(3)-ol-(2)；cis-5,5-Dimethyl-hexen-(3)-ol-(2)；5,5-dimethyl-hex-3c-en-2-ol
• CAS: 2747-56-0
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: ZOQNSGFAAIUNOP-WAYWQWQTSA-N

物化性质

• 沸点：
  74.1 °C(Press: 26 Torr)
• 密度：
  0.842±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：
  2
• 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：

  (Z)-5,5-dimethylhex-3-en-2-ol 在 (TBA)2[SeO4{WO(O2)2}2] 、 双氧水 作用下， 以 氘代乙腈 、 水 为溶剂， 反应 5.0h， 以85%的产率得到(R)-1-((2S,3R)-3-tert-Butyl-oxiranyl)-ethanol
  参考文献：
  名称：

  Kamata, Keigo; Hirano, Tomohisa; Kuzuya, Shinjiro, Journal of the American Chemical Society, 2009, vol. 131, p. 6997 - 7004

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-5,5-dimethylhex-3-yn-2-ol 在 吡啶 、 palladium on activated charcoal 、 Lindlar's catalyst 作用下， 生成 (Z)-5,5-dimethylhex-3-en-2-ol
  参考文献：
  名称：

  Heilmann et al., Bulletin de la Societe Chimique de France, 1957, p. 119,122

  摘要：

  DOI：

文献信息

• Regio- and Diastereoselective Catalytic Epoxidation of Acyclic Allylic Alcohols with Methyltrioxorhenium:  A Mechanistic Comparison with Metal (Peroxy and Peroxo Complexes) and Nonmetal (Peracids and Dioxirane) Oxidants
  作者：Waldemar Adam、Catherine M. Mitchell、Chantu R. Saha-Möller

  DOI：10.1021/jo9902289

  日期：1999.5.1

  Geraniol and its 1-methyl derivative (regiochemical probes) and a set of methyl- and tert-butyl-substituted chiral allylic alcohols (stereochemical probes) have been used to elucidate the mechanism of the MTO-catalyzed epoxidation of allylic alcohols. The regiochemical probes are preferentially epoxidized at the unfunctionalized double bond by these MTO-based oxidants, which establishes that MTO/UHP

  香叶醇及其1-甲基衍生物（区域化学探针）和一组甲基和叔丁基取代的手性烯丙基醇（立体化学探针）已用于阐明MTO催化的烯丙基醇环氧化的机理。区域化学探针优先通过这些基于MTO的氧化剂在未官能化的双键上环氧化，从而确定MTO / UHP和MTO / H（2）O（2）/吡啶主要通过氢键起作用。与过渡金属氧化剂VO（acac）（2）/ t-BuOOH，Mo（CO）（6）/ t-BuOOH，MoO（2）[PhCON（Ph ）O]（2）/ t-BuOOH，MoO（O（2））[PhCON（Ph）O]（2）和H（2）WO（4）/ H（2）O（2）。对于立体化学探针，非对映选择性数据显示MTO催化系统（MTO / UHP和MTO / H（2）O（2）/吡啶）与过水合物型氧化剂Ti-beta / H（2）O（2）和过酸m-CPBA。通过1，3-烯丙基应变的构象控制导致高的苏非对映选择性，其中羟基官能度和and催
• Diastereoselective Catalytic Epoxidation of Chiral Allylic Alcohols by the TS-1 and Ti-β Zeolites:  Evidence for a Hydrogen-Bonded, Peroxy-Type Loaded Complex as Oxidizing Species
  作者：Waldemar Adam、Avelino Corma、T. Indrasena Reddy、Michael Renz

  DOI：10.1021/jo970364i

  日期：1997.5.1

  The similar diastereoselectivities as for peracids implicate a pentacoordinated metal peroxy species in the epoxidation of chiral allylic alcohols by the titanium-containing zeolites TS-1 and Ti-beta. In the loaded complex, the allylic alcohol substrate is fixed through hydrogen bonding to the metal center, with A(1,3) strain as the dominant conformational feature. By comparison of the diastereoselectivities to those for VO(acac)(2)/t-BuOOH, we exclude a peroxy-type complex with direct coordination of the allylic alcohol to the titanium center by means of metal-alcoholate bonding. Neither does a peroxo-type titanium complex apply, as confirmed by comparing the diastereoselectivities with those observed for dioxiranes. With the help of tert-butyl-substituted allylic alcohols as substrates, which are not epoxidized by the TS-1 but by the Ti-beta catalyst, it was unequivocally confirmed that the oxidation occurs inside of the zeolite and not on the outer surface.
• Samarium-promoted cyclopropanation of allylic alcohols
  作者：Gary A. Molander、Lori S. Harring

  DOI：10.1021/jo00276a008

  日期：1989.7
• Lanthanides in organic synthesis. 7. Samarium-promoted, stereocontrolled cyclopropanation reactions
  作者：Gary A. Molander、Jeffrey B. Etter

  DOI：10.1021/jo00226a049

  日期：1987.8
• MOLANDER, GARY A.;HARRING, LORI S., J. ORG. CHEM., 54,(1989) N5, C. 3525-3532
  作者：MOLANDER, GARY A.、HARRING, LORI S.

  DOI：——

  日期：——