(1Z)-3-methyl-1-(2',2',6'-trimethylcyclohex-1'-enyl)-1-penten-4-yn-3-ol | 83060-53-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1Z)-3-methyl-1-(2',2',6'-trimethylcyclohex-1'-enyl)-1-penten-4-yn-3-ol
• 英文别名: (7Z)-9-ethynyl-β-ionol；(Z)-3-methyl-1-(2,6,6-trimethylcyclohexen-1-yl)pent-1-en-4-yn-3-ol
• CAS: 83060-53-1
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: NDGRVUREWSEVSY-LUAWRHEFSA-N

物化性质

• 沸点：
  316.1±22.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (1Z)-3-methyl-1-(2',2',6'-trimethylcyclohex-1'-enyl)-1-penten-4-yn-3-ol 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1,3,3-Trimethyl-2-((E)-3-methyl-nona-1,3,4-trienyl)-cyclohexene
  参考文献：
  名称：

  Electrocyclization of 1-allenyldienes: novel synthesis of drimatrienes and related trans-decalins

  摘要：

  DOI：

  10.1021/ja00386a047
• 作为产物：
  描述：

  (7E)-9-ethynyl-β-ionol 在 2-萘乙酮 作用下， 以 苯 为溶剂， 反应 15.0h， 以94%的产率得到(1Z)-3-methyl-1-(2',2',6'-trimethylcyclohex-1'-enyl)-1-penten-4-yn-3-ol
  参考文献：
  名称：

  Allenyldiene electrocyclization, a stereospecific tandem center-axis-center chirality transfer: synthesis of drimatrienes and related trans-decalins

  摘要：

  DOI：

  10.1021/ja00290a047

文献信息

• [EN] SELECTIVE HYDROGENATION OF ALKYNOLS TO ALKENOLS IN THE PRESENCE OF A PHOSPHORUS COMPOUND<br/>[FR] HYDROGÉNATION SÉLECTIVE D'ALKYNOLS EN ALCÉNOLS EN PRÉSENCE D'UN COMPOSÉ DE PHOSPHORE
  申请人：DSM IP ASSETS BV

  公开号：WO2020239720A1

  公开（公告）日：2020-12-03

  The present invention relates to a process of hydrogenating an aIkynoI selectively to an alkenol by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive which is an organic phosphorus compound bearing either a phosphine or a phosphine oxide group and with the proviso that if the additive bears a phosphino group that the additive bears two or more phosphino groups.

  本发明涉及一种利用钯负载在载体上的氢化催化剂，在有机磷化合物作为添加剂的存在下，通过氢气选择性地将炔烃氢化为烯醇的过程，其中该有机磷化合物带有膦或膦氧化物基团，但需注意如果添加剂带有膦基团，则该添加剂需带有两个或更多膦基团。
• Photosensitized Oxygenation of Twisted 1,3-Dienes:  Abnormally Higher Reactivity of Vinyl Hydrogen Rather than Allyl Hydrogen toward Singlet Oxygen
  作者：Hajime Mori、Keiichi Ikoma、Sachihiko Isoe、Kazuo Kitaura、Shigeo Katsumura

  DOI：10.1021/jo980955o

  日期：1998.11.1

  As one of the novel examples to investigate the characteristic reactivity of significantly twisted 1,3-dienes, the photosensitized oxygenation of two types of significantly twisted 1,3-dienes, cis-beta-ionol derivative 2 and acyclic derivative Il, is investigated. Photosensitized oxygenation of 2a-f and 11a-e revealed that the vinyl hydrogen Ha was more reactive than the allyl hydrogen Hb. Thus, phenyl derivative 2e and tert-butyl-substituted compound lid selectively produced allenes 3e and 13d in 67% and 75% yield resulting from the ene reaction of the vinyl hydrogen Ha rather than allyl alcohols 4e and 14d resulting from the allyl hydrogen abstraction in 24% and 8% yield, respectively. Furthermore, in the case of methyl-substituted compound 11b, the extent of the inherent reactivity of the vinyl hydrogen Ha was similar to that of the allyl hydrogen He. On the basis of X-ray analysis and NIM and MO calculations, the discovered abnormally higher reactivity of the vinyl hydrogen would be rationalized by considering mainly the large sigma*-pi orbital interaction between the vinyl C-H bond and another double bond in significantly twisted 1,3-dienes resulting from calculations of HOMO electron densities.
• SELECTIVE HYDROGENATION OF ALKYNOLS TO ALKENOLS IN THE PRESENCE OF A PHOSPHORUS COMPOUND
  申请人：DSM IP Assets B.V.

  公开号：EP3976569A1

  公开（公告）日：2022-04-06
• SELECTIVE HYDROGENATION OF ALKYNES TO ALKENES IN THE PRESENCE OF A PHOSPHORUS COMPOUND AND AN ORGANIC SULPHUR COMPOUND
  申请人：DSM IP ASSETS B.V.

  公开号：US20220242807A1

  公开（公告）日：2022-08-04

  The present invention relates to a process of hydrogenating an alkyne selectively to an alkene by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive mixture of an organic phosphorus compound (AP) and an organic sulphur compound (AS).
• [EN] SELECTIVE HYDROGENATION OF ALKYNES TO ALKENES IN THE PRESENCE OF A PHOSPHORUS COMPOUND AND AN ORGANIC SULPHUR COMPOUND<br/>[FR] HYDROGÉNATION SÉLECTIVE D'ALCYNES EN ALCÈNES EN PRÉSENCE D'UN COMPOSÉ PHOSPHORÉ ET D'UN COMPOSÉ SOUFRÉ ORGANIQUE
  申请人：DSM IP ASSETS BV

  公开号：WO2020239721A1

  公开（公告）日：2020-12-03

  The present invention relates to a process of hydrogenating an alkyne selectively to an alkene by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive mixture of an organic phosphorus compound (AP) and an organic sulphur compound (AS).