3,3aα,6,6aα-tetrahydro-2(1H)-pentalenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3aα,6,6aα-tetrahydro-2(1H)-pentalenone
• 英文别名: bicyclo<3.3.0>oct-2-en-7-one；bicyclo<3.3.0>oct-6-en-3-one；Bicyclo<3.3.0>octenon；cis-bicyclo[3.3.0]oct-6-ene-3-one；Bicyclo<3.3.0>oct-6-en-3-on；(3aR,6aS)-3,3a,4,6a-tetrahydro-1H-pentalen-2-one
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: CRMVPSCZISTVFY-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3aα,6,6aα-tetrahydro-2(1H)-pentalenone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (+)-(1R,5S,7R)-bicyclo[3.3.0]oct-2-en-7-ol
  参考文献：
  名称：

  Demuth, Martin; Schaffner, Kurt, Angewandte Chemie, 1982, vol. 94, # 11, p. 809 - 825

  摘要：

  DOI：
• 作为产物：
  描述：

  bicyclo[2.2.2]oct-2-ene 在 氢氧化钾 、 Nafion-TMS 、 五氯化磷 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 3,3aα,6,6aα-tetrahydro-2(1H)-pentalenone
  参考文献：
  名称：

  Demuth, Martin; Schaffner, Kurt, Angewandte Chemie, 1982, vol. 94, # 11, p. 809 - 825

  摘要：

  DOI：

文献信息

• Bicyclooctanes: cis-bicyclo[3.3.0]octa-2,6 and 2,7-diene-2-carboxylic acids
  作者：James K. Whitesell、Mark A. Minton、William G. Flanagan

  DOI：10.1016/0040-4020(81)80012-9

  日期：1981.1

  Two independent routes to each of the title acids, useful in the synthesis of natural products, are presented. The sequences commence with readily available materials which are amenable to the preparation of multigram quantities. Complete 13C spectral data is supplied for intermediates and products.

  给出了两种标题酸的独立途径，可用于合成天然产物。序列以易于获得的材料开始，这些材料适合于制备多克级数。提供了中间体和产品的完整13 C光谱数据。
• Syntheses and biological evaluation of vinblastine congeners
  作者：Martin E. Kuehne、William G. Bornmann、Istvan Markó、Yong Qin、Karen L. LeBoulluec、Deborah A. Frasier、Feng Xu、Tshilundu Mulamba、Carol L. Ensinger、Linda S. Borman、Anne E. Huot、Christopher Exon、Fred T. Bizzarro、Julia B. Cheung、Susan L. Bane

  DOI：10.1039/b209990j

  日期：——

  Sixty-two congeners of vinblastine (VLB), primarily with modifications of the piperidine ring in the carbomethoxycleavamine moiety of the binary alkaloid, were synthesized and evaluated for cytotoxicity against murine L1210 leukemia and RCC-2 rat colon cancer cells, and for their ability to inhibit polymerization of microtubular protein at <10−6 M, and for induction of spiralization of microtubular protein, and for microtubular disassembly at 10−4 M concentrations. An ID50 range of >107 M concentrations was found for L1210 inhibition by these compounds, with the most active 1000× as potent as vinblastine.

  合成了长春碱（VLB）的62个类似物，主要是通过改变二元生物碱中碳甲氧基克拉维胺部分的哌啶环来修改结构，并评估了它们对小鼠L1210白血病和大鼠RCC-2结肠癌细胞的细胞毒性，以及它们在<10^-6 M浓度下抑制微管蛋白聚合、诱导微管蛋白螺旋化和在10^-4 M浓度下解聚微管的能力。这些化合物对L1210的抑制作用表现出>10^7 M的ID50范围，其中最活跃的化合物比长春碱的效力高出1000倍。
• A practical route to both enantiomers of bicyclo[3.3.0]oct-2-en-7-one and their use for the synthesis of key trisubstituted cyclopentanes
  作者：David Cousin、John Mann

  DOI：10.1016/j.tet.2008.01.134

  日期：2008.4

  We describe new methodology for the synthesis of both enantiomers of 7,7-dichlorobicyclo[3.2.0]hep-2-en-6-one and conversion of these compounds into stereochemically defined bicyclo[3.3.0]oct-2-en-7-ones and thence trisubstituted cyclopentanes. These are key intermediates for the synthesis of prostanoids, brefeldin and other cyclopentane-containing natural products.

  我们描述了7,7-二氯双环[3.2.0] hep-2-en-6-one的两个对映异构体的合成以及将这些化合物转化为立体化学定义的双环[3.3.0] oct-2-en-的新方法7-ones，然后是三取代的环戊烷。这些是合成前列腺素，布雷菲德菌素和其他含环戊烷的天然产物的关键中间体。
• Valence isomers of azulene and heptalene
  作者：Ichiro Murata、Yoshixkazu Sugihara、Takashi Sugimura、Shigeharu Wakabayashi

  DOI：10.1016/s0040-4020(01)87592-x

  日期：——

  Synthetic methods for the valene type valence isomers6a,b and Dewar type isomers 7a,b of azulene have been elaborated utilizing the same intermediate 12a. Cyano-Dewar heptalene 9 has also been synthesized. Thermal and photochemical isomerizations of these prototype molecules are discussed briefly.

  利用相同的中间体12a，已经详细说明了z烯的戊烯型价异构体6a，b和杜瓦型异构体7a，b的合成方法。也已经合成了氰基杜瓦庚烯9。简要讨论了这些原型分子的热和光化学异构化。
• Regio- and Stereoselective Functionalizations of Tricyclo [3.3.0.02,8]octan-3-one, a Potential Synthon for Polycyclopentanoid Terpenes and Prostacyclin Analogs. Preliminary Communication
  作者：Martin Demuth、Sosale Chandrasekhar、Koichi Nakano、Palaykotai R. Raghavan、Kurt Schaffner

  DOI：10.1002/hlca.19800630837

  日期：1980.12.10

  transformation of tricyclo [3.3.0.02,8]octan-3-one (1) have been carried out in order to explore its potential utility as a versatile synthon for polycyclopentanoid terpenes and prostacyclin analogs. Various functionalizations of rings A and B and annulation of a third ring C were achieved in generally high yields. The system provides for a large measure of regio- and stereoselective reaction control

  为了探索其作为多环戊烷萜烯和前列环素类似物的通用合成子的潜在用途，已进行了三环[3.3.0.0 2,8 ] octan -3-one （1）的化学转化。通常以高收率实现环A和B的各种官能化以及第三环C的环化。该系统提供了大量的区域和立体选择性反应控制。