(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraenylidene]-1,5,5-trimethylcyclohexene | 1224-78-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: (6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraenylidene]-1,5,5-trimethylcyclohexene
• 英文别名: anhydroretinol；Anhydrovitamin A
• CAS: 1224-78-8；7245-10-5；20603-89-8；70268-03-0；70268-04-1；70268-05-2；144407-18-1
• 化学式: C₂₀H₂₈
• 分子量: 268.442
• InChiKey: FWNRILWHNGFAIN-IBMYPUIMSA-N

物化性质

• 熔点：
  65-70°C
• 沸点：
  378.4±9.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、乙酸乙酯（轻微）、甲醇（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

制备方法与用途

生物活性

all-trans-Anhydro Retinol (Anhydrovitamin A) 是维生素 A 的代谢产物。all-trans-Anhydro Retinol 用于合成的多种维生素制剂。

靶点

Human Endogenous Metabolite

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 、 苯 作用下， 生成 (6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraenylidene]-1,5,5-trimethylcyclohexene
  参考文献：
  名称：

  Shantz, Journal of Biological Chemistry, 1950, vol. 182, p. 515,520

  摘要：

  DOI：

文献信息

• Intramolecular Diels-Alder reactions of the retinoid side chain
  作者：Y. Fulmer Shealy、James M. Riordan、Jerry L. Frye、Sheila R. Campbell

  DOI：10.1016/0040-4020(95)00898-5

  日期：1996.1

  Retinyl propynyl ether (RPE) undergoes an intramolecular Diels-Alder reaction to form a tetrahydroisobenzofuran derivative by addition of the alkyne group at positions 11 and 14 of the retinoid side chain. The Diels-Alder product can be isolated after RPE has been heated in refluxing ethanol. The Diels-Alder reaction also occurs very slowly in the solid state at low temperatures. The tetrahydroisobenzofuran

  视黄基丙炔基醚（RPE）进行分子内Diels-Alder反应，通过在类视黄醇侧链的11和14位上添加炔基，形成四氢异苯并呋喃衍生物。RPE在回流的乙醇中加热后，即可分离出Diels-Alder产品。在低温下，固态的Diels-Alder反应也非常缓慢地发生。四氢异苯并呋喃易于脱氢成芳族类维生素A，1，3-二氢异苯并呋喃。2-丁炔基和2-丙烯基视黄基醚经过分子内环化反应，生成类似于Diels-Alder的产物，在回流的甲苯中加热醚后，其分离率为50–60％。
• Ionic photodissociation of polyenes via a highly polarized singlet excited state
  作者：A. Mahipal Reddy、V. Jayathirtha Rao

  DOI：10.1021/jo00051a011

  日期：1992.12

  Several polyene acetates and polyene methyl ether were prepared. Upon direct excitation these polyenes undergo ionic photodissociation from their singlet excited states. Triplet-sensitization experiments on these polyenes revealed that the ionic photodissociation process is restricted to singlet excited states. The rationale put forward is that the polyene chromophore undergoes charge separation/polarization in the singlet excited state, which leads to ionic photodissociation.
• Waldmann, Doris; Koenig, Thorsten; Schreier, Peter, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 4, p. 589 - 594
  作者：Waldmann, Doris、Koenig, Thorsten、Schreier, Peter

  DOI：——

  日期：——
• Stereocontrolled synthesis of all-(E)- and (8Z)-anhydroretinol
  作者：Rosana Alvarez、Beatriz Iglesias、Susana López、Angel R. de Lera

  DOI：10.1016/s0040-4039(98)01101-0

  日期：1998.7

  Convergent syntheses of hexaenes anhydroretinol and its (8Z)-isomer are described. Despite the mild reaction conditions for the final step in both cases, a Stille coupling reaction between trienyl triflates and trienyl stannanes, the stereochemical integrity of anhydroretinol is not maintained, due to its intrinsic instability. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Regioselective photo isomerisation of retinolacetate
  作者：V Jayathirtha Rao、U.T Bhalerao

  DOI：10.1016/s0040-4039(00)97417-3

  日期：1990.1