(7S,8R,8'R)-9-O-acetyldihydrosesamin | 28071-35-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (7S,8R,8'R)-9-O-acetyldihydrosesamin
• 英文别名: Dihydrosesamin acetate；[(2S,3R,4R)-2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)oxolan-3-yl]methyl acetate
• CAS: 28071-35-4；128822-11-7；133576-09-7
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: YXTPTAIGIJPTGR-PNLZDCPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 (7S,8R,8'R)-9-O-acetyldihydrosesamin 在 氢氧化钾 作用下， 生成 deoxypicropodophyllinic acid methyl ester
  参考文献：
  名称：

  杜松极性提取物中的木脂素

  摘要：

  摘要 从杜松叶氯仿提取物中分离鉴定出3种新的天然木脂素，即脱氧鬼臼毒素甲酯、鬼臼毒素酸和7β-羟基二氢芝麻素，11种已知木脂素和2种肉桂醇。β-甲基peltatin B 的 13 C NMR 光谱的分配也通过直接和远程异核 2D 核磁共振分析进行，修改了以前的分配。

  DOI：

  10.1016/0031-9422(91)83051-l
• 作为产物：
  描述：

  二氢荜澄茄脂素 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 (7S,8R,8'R)-9-O-acetyldihydrosesamin
  参考文献：
  名称：

  Oxidative transformations of lignans - reactions of dihydrocubebin and a derivative with DDQ

  摘要：

  Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound (8) and the aryl tetralin (9), while with DDQ in trifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.

  DOI：

  10.1016/s0040-4020(01)86384-5

文献信息

• Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)
  作者：Masanori Kuroyanagi、Ryuya Ikeda、Hui Yuan Gao、Norio Muto、Keisuke Otaki、Toshikazu Sano、Nobuo Kawahara、Takahisa Nakane

  DOI：10.1248/cpb.56.60

  日期：——

  In the screening of biologically active constituents from woody plants, the methanol extract of leaves of Chamaecyparis obtusa showed potent neurite outgrowth-promoting activity in neuronal PC12 cells. The ethyl acetate-soluble fraction of the methanol extract showed potent activity and was separated by means of various chromatographic methods to give the two new compounds 1 and 2, as well as 11 known lignan and sesquiterpene derivatives. The structures of the new compounds were determined to be 9-O-acetyldihydrosesamin (1) and 9-O-(11-hydroxyeudesman-4-yl)dihydrosesamin (2), respectively, in NMR studies including 2D-NMR experiments. Of the 13 compounds, the known compound hinokinin (5) and the new compound 2 showed potent neurite outgrowth-promoting activity in PC 12 cells.

  在木本植物生物活性成分的筛选中，日本扁柏叶的甲醇提取物在神经元 PC12 细胞中显示出有效的神经突生长促进活性。甲醇提取物的乙酸乙酯可溶部分显示出有效的活性，并通过各种色谱方法分离得到两种新化合物1和2，以及11种已知的木酚素和倍半萜衍生物。在包括 2D-NMR 实验在内的 NMR 研究中，新化合物的结构分别确定为 9-O-乙酰基二氢芝麻素 (1) 和 9-O-(11-羟基eudesman-4-基)二氢芝麻素 (2)。在 13 种化合物中，已知化合物 hinokinin (5) 和新化合物 2 在 PC 12 细胞中显示出有效的神经突生长促进活性。
• Synthesis of the lignan (±)-dihydrosesamin: problems of stereocontrol in the formation of 2,3,4-trisubstituted tetrahydrofurans and tetrahydrofuranones
  作者：David R. Stevens、Donald A. Whiting

  DOI：10.1039/p19900000425

  日期：——

  It is shown that the stereochemistry of addition reactions to 3-arylidene lactones (3) and (9) is controlled by the 5- rather than the 4-substituent: synthesis of the 2,3-trans 3,4-cis lignan dihydrosesamin (11) thus requires use of the 4,5-cis lactone (8), with epimerisation at C-2 following establishment of 3,4-cis geometry.

  结果表明，3-芳基内酯（3）和（9）的加成反应的立体化学是由5-取代基而不是4-取代基控制的：2,3-反式3,4-顺式木脂素二氢芝麻素（因此，11）需要使用4,5-顺式内酯（8），并在建立3,4-顺式几何构型后在C-2上差向异构化。
• Stevens, David R.; Whiting, Donald A., Journal of the Chemical Society. Perkin transactions I, 1992, # 5, p. 633 - 637
  作者：Stevens, David R.、Whiting, Donald A.

  DOI：——

  日期：——
• Lignans from polar extracts ofJuniperus thurifera
  作者：Arturo San Feliciano、Jose M. Miguel Del Corral、Jose L. Lopez、Beatriz De Pascual-Teresa

  DOI：10.1016/0031-9422(91)83051-l

  日期：1992.1

  Abstract Three new natural lignans, methyl deoxypodophyllotoxinate, podophyllotoxinic acid and 7β-hydroxydihydrosesamin, 11 known lignans and two cinnamyl alcohols were isolated and identified from a chloroform extract of Juniperus thurifera leaves. Assignment of the 13 C NMR spectrum of β-methyl peltatin B was also performed through direct and long-range heteronuclear 2D NMR analysis, amending previous

  摘要 从杜松叶氯仿提取物中分离鉴定出3种新的天然木脂素，即脱氧鬼臼毒素甲酯、鬼臼毒素酸和7β-羟基二氢芝麻素，11种已知木脂素和2种肉桂醇。β-甲基peltatin B 的 13 C NMR 光谱的分配也通过直接和远程异核 2D 核磁共振分析进行，修改了以前的分配。
• Oxidative transformations of lignans - reactions of dihydrocubebin and a derivative with DDQ
  作者：Andrew Pelter、Robert S. Ward、Revuru Venkateswarlu、Chakicherla Kamakshi

  DOI：10.1016/s0040-4020(01)86384-5

  日期：1991.1

  Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound (8) and the aryl tetralin (9), while with DDQ in trifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.