(1S,3aR,5R,5aR,8aR,9S,9aS)-9-羟基-1,5,8a-三甲基-3a,4,5,5a,9,9a-六氢-1H-薁并[7,6-D]呋喃-2,8-二酮 | 34257-95-9

• 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: (1S,3aR,5R,5aR,8aR,9S,9aS)-9-羟基-1,5,8a-三甲基-3a,4,5,5a,9,9a-六氢-1H-薁并[7,6-D]呋喃-2,8-二酮
• 英文名称: plenolin
• 英文别名: 11α,13-dihydrohelenalin；Dihydrohelenalin；(1S,3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione
• CAS: 34257-95-9
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: ICKWITMQEROMDG-ZIXXKTFOSA-N

物化性质

• 熔点：
  224.5°C
• 沸点：
  327.55°C (rough estimate)
• 密度：
  1.0583 (rough estimate)
• LogP：
  1.980 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1(b)

反应信息

• 作为反应物：
  描述：

  (1S,3aR,5R,5aR,8aR,9S,9aS)-9-羟基-1,5,8a-三甲基-3a,4,5,5a,9,9a-六氢-1H-薁并[7,6-D]呋喃-2,8-二酮 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 乙醇 、 苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  抗肿瘤药XXXVI：倍半萜烯内酯微Helenins-A，B和C，醋酸微列宁和小脑Helenium的培林脂的结构解析。

  摘要：

  从Helenium microcephalum中分离出抗肿瘤倍半萜烯内酯微Helenins-A，B和C，醋酸微列宁和Plenolin。这些内酯的结构和立体化学通过物理方法以及化学转化和相关性来确定。醋酸微列宁似乎是第一个被证明具有显着抗白血病活性的新型二聚倍半萜内酯。

  DOI：

  10.1002/jps.2600690916
• 作为产物：
  描述：

  心菊内酯 在 nickel boride 氢气 作用下， 以 乙醇 为溶剂， 以500 mg的产率得到(1S,3aR,5R,5aR,8aR,9S,9aS)-9-羟基-1,5,8a-三甲基-3a,4,5,5a,9,9a-六氢-1H-薁并[7,6-D]呋喃-2,8-二酮
  参考文献：
  名称：

  Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents

  摘要：

  Bis(helenalinyl), bis(plenolinyl), bis(2,3-dihydrohelenalinyl), and bis(2,3,11,13-tetrahydrohelenalinyl) esters have been synthesized in an effort to elucidate the role of the two enone alkylating centers, beta-unsubstituted cyclopentenone and alpha-methylene gamma-lactone, as well as the significance of the diester linkage with respect to the enhanced in vivo P-388 lymphocytic leukemia antileukemic activity of bis(helenalinyl) malonate (2) against P-388 lymphocytic leukemia in the mouse. The bisesters (2-5; 7, 8; 10, 11) are, in general, more potent and less toxic than their corresponding parent alcohols (1, 6; 9; 14). The beta-unsubstituted cyclopentenone ring and the alpha-methylene gamma-lactone moiety in the bisesters play important roles for the enhancement of the P-388 antileukemic activity. Removal of the enone double bonds in both alkylating centers of 2 gave rise to inactive compounds. Except for 2, the potent antileukemic activity of the bis(helenalinyl) esters (3-5) appears to be independent of the ester chain length.

  DOI：

  10.1021/jm00140a003

文献信息

• Helenalin. III. Reduction and Dehydrogenation
  作者：Roger. Adams、Werner. Herz

  DOI：10.1021/ja01175a089

  日期：1949.7
• Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents
  作者：Kuo-Hsiung Lee、Toshiro Ibuka、Donald Sims、Osamu Muraoka、Hiroshi Kiyokawa、Iris H. Hall、Hyeong L. Kim

  DOI：10.1021/jm00140a003

  日期：1981.8

  Bis(helenalinyl), bis(plenolinyl), bis(2,3-dihydrohelenalinyl), and bis(2,3,11,13-tetrahydrohelenalinyl) esters have been synthesized in an effort to elucidate the role of the two enone alkylating centers, beta-unsubstituted cyclopentenone and alpha-methylene gamma-lactone, as well as the significance of the diester linkage with respect to the enhanced in vivo P-388 lymphocytic leukemia antileukemic activity of bis(helenalinyl) malonate (2) against P-388 lymphocytic leukemia in the mouse. The bisesters (2-5; 7, 8; 10, 11) are, in general, more potent and less toxic than their corresponding parent alcohols (1, 6; 9; 14). The beta-unsubstituted cyclopentenone ring and the alpha-methylene gamma-lactone moiety in the bisesters play important roles for the enhancement of the P-388 antileukemic activity. Removal of the enone double bonds in both alkylating centers of 2 gave rise to inactive compounds. Except for 2, the potent antileukemic activity of the bis(helenalinyl) esters (3-5) appears to be independent of the ester chain length.
• Antitumor Agents XXXVI: Structural Elucidation of Sesquiterpene Lactones Microhelenins-A, B, and C, Microlenin Acetate, and Plenolin from Helenium microcephalum
  作者：Yasuhiro Imakura、Kuo-Hsiung Lee、Donald Sims、Rong-Yang Wu、Iris H. Hall、Hiroshi Furukawa、Masataka Itoigawa、Kazue Yonaha

  DOI：10.1002/jps.2600690916

  日期：1980.9

  The antitumor sesquiterpene lactones microhelenins-A, B, and C, microlenin acetate, and plenolin were isolated from Helenium microcephalum. The structures and stereochemistry of these lactones were determined by physical methods as well as by chemical transformations and correlations. Microlenin acetate appears to be the first novel dimeric sesquiterpene lactone demonstrated to have significant antileukemic

  从Helenium microcephalum中分离出抗肿瘤倍半萜烯内酯微Helenins-A，B和C，醋酸微列宁和Plenolin。这些内酯的结构和立体化学通过物理方法以及化学转化和相关性来确定。醋酸微列宁似乎是第一个被证明具有显着抗白血病活性的新型二聚倍半萜内酯。