(E)-5,9-二甲基-4,8-癸二烯-1-醇 | 67858-88-2

• 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
• 中文名称: (E)-5,9-二甲基-4,8-癸二烯-1-醇
• 英文名称: (E)-5,9-dimethyldeca-4,8-dien-1-ol
• 英文别名: 5,9-dimethyl-4(E),8-decadien-1-ol；(4E)-5,9-dimethyldeca-4,8-dien-1-ol
• CAS: 67858-88-2
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: FBHDDQNBWXRPSP-XYOKQWHBSA-N

物化性质

• 沸点：
  273.2±9.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (E)-5,9-二甲基-4,8-癸二烯-1-醇 在 吡啶 、 sodium iodide 作用下， 生成 <(E)-5,9-Dimethyl-4,8-decadienyl>triphenylphosphonium iodide
  参考文献：
  名称：

  Squalene synthetase. Inhibition by an ammonium analogue of a carbocationic intermediate in the conversion of presqualene pyrophosphate to squalene

  摘要：

  DOI：

  10.1021/ja00389a106
• 作为产物：
  描述：

  (E)-5,9-dimethyldeca-4,8-dienenitrile 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 生成 (E)-5,9-二甲基-4,8-癸二烯-1-醇
  参考文献：
  名称：

  Synthesis of Curcumanolide A, a Unique Spirolactone Sesquiterpene

  摘要：

  利用 Br+ 诱导的环化和随后的缩环法，通过 11 个步骤从高香叶基氰化物合成了外消旋形式的螺环内酯--莪术内酯 A。

  DOI：

  10.1246/cl.1992.2343

文献信息

• Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton‐Coupled Electron Transfer
  作者：Elaine Tsui、Anthony J. Metrano、Yuto Tsuchiya、Robert R. Knowles

  DOI：10.1002/anie.202003959

  日期：2020.7.13

  We report a catalytic, light‐driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible‐light irradiation in the presence of an IrIII‐based photoredox catalyst, a Brønsted base catalyst, and a hydrogen‐atom transfer (HAT) co‐catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct

  我们报告了一种催化光驱动方法，用于未活化烯醇的分子内加氢醚化以提供环醚产品。这些反应在 Ir III基光氧化还原催化剂、布朗斯台德碱催化剂和氢原子转移 (HAT) 助催化剂存在下在可见光照射下发生。反应性烷氧基被认为是关键中间体，是通过质子耦合电子转移机制直接均裂激活醇 O−H 键而产生的。该方法表现出广泛的底物范围和高官能团耐受性，并且适应多种烯烃取代模式。还提出了证明该催化系统扩展到碳醚化反应的结果。
• Methods of using .alpha.-phosphonosulfonate squalene synthetase
  申请人：Bristol-Myers Squibb Company

  公开号：US05470845A1

  公开（公告）日：1995-11-28

  .alpha.-Phosphonosulfonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2 is OR.sup.5 or R.sup.5a ; R.sup.3 and R.sup.5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R.sup.5a is H, alkyl, arylalkyl or aryl; R.sup.4 is H, alkyl, aryl, arylalkyl, or cycloalkyl;, Z is H, halogen, lower alkyl or lower alkenyl; and R.sup.1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; as further defined above; including pharmaceutically acceptable salts and or prodrug esters of the phosphonic (phosphinic) and/or sulfonic acids.

  提供了抑制酶角鲨烯合酶并从而抑制胆固醇生物合成的.alpha.-磷酸磺酸酯化合物。这些化合物的化学式为##STR1##其中R.sup.2为OR.sup.5或R.sup.5a；R.sup.3和R.sup.5独立地为H、烷基、芳基烷基、芳基或环烷基；R.sup.5a为H、烷基、芳基烷基或芳基；R.sup.4为H、烷基、芳基、芳基烷基或环烷基；Z为H、卤素、低烷基或低烯基；R.sup.1为至少含有7个碳原子的疏水基团，为烷基、烯基、炔基、混合烯基-炔基、芳基、芳基烷基、环烷基、环烷基烷基、杂环芳基、杂环芳基烷基、环杂环烷基、环杂环烷基烷基；如上所述；包括磷酸(亚磷酸)和/或磺酸的药用可接受盐和/或前药酯。
• .alpha.-phosphonocarboxylate squalene synthetase inhibitors
  申请人：Bristol-Myers Squibb Co.

  公开号：US05312814A1

  公开（公告）日：1994-05-17

  .alpha.- Phosphonocarboxylate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.1 is a lipophilic group which contains at least 7 carbons and is substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted arylalkyl or optionally substituted aryl; Z is H, halogen, hydroxy, hydroxyalkyl or lower alkyl; R.sup.2 and R.sup.3 are independently H, metal ion or other pharmaceutically acceptable cation, or a prodrug ester; R.sup.4 is H, metal ion or other pharmaceutically acceptable cation, lower alkyl, lower alkenyl, arylalkyl, aryl or a prodrug ester.

  提供了抑制齐墩果酸合酶并从而抑制胆固醇生物合成的磷酸羧酸化合物。这些化合物的化学式为##STR1##其中R.sup.1是至少含有7个碳且为取代烷基、可选择取代环烷基、可选择取代环烷基烷基、可选择取代烯基、可选择取代炔基、可选择取代芳基烷基或可选择取代芳基的亲脂基团；Z为H、卤素、羟基、羟基烷基或较低烷基；R.sup.2和R.sup.3独立地为H、金属离子或其他药用可接受阳离子，或为一种前药酯；R.sup.4为H、金属离子或其他药用可接受阳离子、较低烷基、较低烯基、芳基烷基、芳基或一种前药酯。
• Hydroxyphosphinyl phosphonate squalene synthetase inhibitors and method
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05254544A1

  公开（公告）日：1993-10-19

  Hydroxyphosphinyl phosphonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, metal ion or a prodrug ester; and R.sup.1 is a lipophilic group which contains at least 6 carbons and is alkyl, alkenyl, alkynyl, mixed alkenylalkynyl, a hetero-containing moiety as defined herein, or a phenylalkyl or phenylalkenyl group including those containing a biphenyl group.

  提供了抑制齐墩果醇合成酶并从而抑制胆固醇生物合成的羟基膦基膦酸酯化合物。这些化合物的化学式为##STR1##其中R.sup.2、R.sup.3和R.sup.4独立地为H、烷基、金属离子或前药酯；而R.sup.1是至少含有6个碳原子的疏水基团，可以是烷基、烯基、炔基、混合烯基炔基、本文中定义的含杂原子的基团，或者是苯基烷基或苯基烯基基团，包括含有联苯基团的那些基团。
• Bisphosphonate squalene synthetase inhibitors and method
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05157027A1

  公开（公告）日：1992-10-20

  Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents are provided which have the structure ##STR1## and analogs thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are H, lower alkyl, a metal ion or a prodrug ester; R.sup.5 is H, halogen or lower alkyl; Zq is substituted alkenyl, substituted alkynyl, mixed alkenyl-alkynyl or substituted phenylalkyl or, phenylalkenyl or phenylalkynyl, or alkyl, including all stereoisomers thereof. New methods for using such compounds to inhibit cholesterol biosynthesis are also provided.

  提供了一种抑制胆固醇生物合成（通过抑制新生角鲨烯生物合成）的化合物，因此可用作降胆固醇药物和抗动脉粥样硬化药物，其结构为##STR1##及其类似物，其中R.sup.1、R.sup.2、R.sup.3和R.sup.4相同或不同，为H、较低烷基、金属离子或前药酯；R.sup.5为H、卤素或较低烷基；Zq为取代烯基、取代炔基、混合烯基-炔基或取代苯基烷基、苯基烯基或苯基炔基，或烷基，包括其所有立体异构体。还提供了使用这些化合物抑制胆固醇生物合成的新方法。