2-methanesulfonyloxymethyl cyclopentane ethylene ketal | 116802-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methanesulfonyloxymethyl cyclopentane ethylene ketal
• 英文别名: 2-methanesulfonyloxymethylcyclopentanone ethyleneketal；1,4-Dioxaspiro[4.4]nonan-9-ylmethyl methanesulfonate
• CAS: 116802-70-1
• 化学式: C₉H₁₆O₅S
• 分子量: 236.289
• InChiKey: AVNAKFNAGIONJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methanesulfonyloxymethyl cyclopentane ethylene ketal 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 potassium carbonate 、 对甲苯磺酸 、 一水合肼 、 二乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 丙酮 、 二乙二醇 为溶剂， 生成 5-Methylenespiro<3.4>octane
  参考文献：
  名称：

  Cleavage vs. rearrangement ratios and secondary deuterium kinetic isotope effects in the thermolysis of conformationally fixed cisoid vinylcyclobutanes

  摘要：

  The first-order rate constants for the thermally induced retro 2 + 2 cleavage and rearrangement of 5-methylenespiro[3.5]nonane occur in a 1:2 ratio. In contrast, a 2:1 ratio of these rate constants is usual from conformationally unbiased vinylcyclobutanes. Comparison of the activation parameters suggests that the rearrangement in unbiased systems results from an unfavorable entropy of activation which suggests that the rearrangement is concerted. For the rearrangement of 5-methylenespiro[3.4]octane, the secondary deuterium kinetic isotope effect at the exo-methylene carbon (k(H)/k(D)2) is 1.086 +/- 0.023. This is also consistent with concert in the rearrangement where exo-methylene rotation contributes to the reaction coordinate. The secondary KIE for cleavage of 5-methylenespiro[3.4]octane is 1.025 +/- 0.027.

  DOI：

  10.1021/jo00006a006
• 作为产物：
  描述：

  1,4-dioxa-spiro[4.4]nonane-6-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-methanesulfonyloxymethyl cyclopentane ethylene ketal
  参考文献：
  名称：

  Aromatase Inhibitors: Synthesis, Biological Activity, and Structure of 1,2-Imidazolylmethylcyclopentanol Derivatives.

  摘要：

  使用易于获得的甲基2-氧代环戊烷羧酸酯作为起始原料，制备了两系列1,2-二取代咪唑甲基环戊醇衍生物（5a-d, 10a-d）。进行了体外芳香酶抑制活性评估，并与甾体芳香酶抑制剂福美坦和非甾体抑制剂法乐唑进行了活性比较。在这些化合物中，5d、10a、10b、10c、11a、15a和15b的芳香酶抑制活性比福美坦更强。特别是1-(4-氯苄基)-顺-2-(1H-咪唑-1-基甲基)环戊醇（10a）被鉴定为强效体外芳香酶抑制剂，显示IC50值为4×10^-8M。10a的对映体被分离，并通过X射线晶体学确定了其绝对构型。

  DOI：

  10.1248/cpb.43.2152

文献信息

• Novel azole derivative and agricultural/horticultural fungicide
  申请人：Kureha Kagaku Kogyo Kabushiki Kaisha

  公开号：US04902702A1

  公开（公告）日：1990-02-20

  An azole derivative represented by the formula (I): ##STR1## wherein X and Y independently represent a halogen atom, a phenyl group or a hydrogen atom, providing that at least one of X and Y is not a hydrogen atom, n represents an integer of 0, 1 or 2, and A represents a nitrogen atom or CH, and an agricultural/horticultural fungicide comprising the azole derivative as an active ingredient are disclosed. The azole derivative exhibits an excellent effect in preventing and curing a wide spectrum of plant diseases and possesses low toxicity to mammals.

  一种由以下式（I）表示的唑类衍生物：##STR1## 其中X和Y分别表示卤素原子、苯基或氢原子，要求至少X和Y中的一个不是氢原子，n代表0、1或2的整数，A代表氮原子或CH，以及包含该唑类衍生物作为活性成分的农业/园艺杀菌剂被披露。该唑类衍生物在预防和治疗各种植物病害方面表现出优异效果，并对哺乳动物具有低毒性。
• EHNARI, XIROYUKI;KUMADZAVA, MASARU;SIMIDZU, SUSUMU;ITO, TOKUSI;SATO, NOBU+
  作者：EHNARI, XIROYUKI、KUMADZAVA, MASARU、SIMIDZU, SUSUMU、ITO, TOKUSI、SATO, NOBU+

  DOI：——

  日期：——
• Aromatase Inhibitors: Synthesis, Biological Activity, and Structure of 1,2-Imidazolylmethylcyclopentanol Derivatives.
  作者：Akira KATO、Yuko IKEDA、Norifumi SUGITA、Toyohiko NITTA、Hiroyuki ENARI、Akiko KASHIMA、Michiko KONNO、Koichi NIIMURA

  DOI：10.1248/cpb.43.2152

  日期：——

  Two series of 1, 2-disubstituted imidazolylmethylcyclopentanol derivatives (5a-d, 10a-d) were prepared by using easily available metyl 2-oxocyclopentanecarboxylate as the starting material. Evaluation of the aromatase inhibitory activities in vitro was performed. Their activities were compared with those of a steroidal aromatase inhibitor, Formestane, and a non-steroidal inhibitor, Fadrozole. Among these compounds, the aromatase inhibitory activities of 5d, 10a, 10b, 10c, 11a, 15a, and 15b were more potent than Formestane. One compound, 1-(4-chlorobenzyl)-cis-2-(1H-imidazol-1-ylmethyl)cyclopentanol (10a) was in particular identified as a potent aromatase inhibitor in vitro, exhibiting an IC50 value of 4×10-8M. The enantiomers of 10a were separated, and their absolute configurations were determined by X-ray crystallography.

  使用易于获得的甲基2-氧代环戊烷羧酸酯作为起始原料，制备了两系列1,2-二取代咪唑甲基环戊醇衍生物（5a-d, 10a-d）。进行了体外芳香酶抑制活性评估，并与甾体芳香酶抑制剂福美坦和非甾体抑制剂法乐唑进行了活性比较。在这些化合物中，5d、10a、10b、10c、11a、15a和15b的芳香酶抑制活性比福美坦更强。特别是1-(4-氯苄基)-顺-2-(1H-咪唑-1-基甲基)环戊醇（10a）被鉴定为强效体外芳香酶抑制剂，显示IC50值为4×10^-8M。10a的对映体被分离，并通过X射线晶体学确定了其绝对构型。
• Cleavage vs. rearrangement ratios and secondary deuterium kinetic isotope effects in the thermolysis of conformationally fixed cisoid vinylcyclobutanes
  作者：J. J. Gajewski、G. C. Paul

  DOI：10.1021/jo00006a006

  日期：1991.3

  The first-order rate constants for the thermally induced retro 2 + 2 cleavage and rearrangement of 5-methylenespiro[3.5]nonane occur in a 1:2 ratio. In contrast, a 2:1 ratio of these rate constants is usual from conformationally unbiased vinylcyclobutanes. Comparison of the activation parameters suggests that the rearrangement in unbiased systems results from an unfavorable entropy of activation which suggests that the rearrangement is concerted. For the rearrangement of 5-methylenespiro[3.4]octane, the secondary deuterium kinetic isotope effect at the exo-methylene carbon (k(H)/k(D)2) is 1.086 +/- 0.023. This is also consistent with concert in the rearrangement where exo-methylene rotation contributes to the reaction coordinate. The secondary KIE for cleavage of 5-methylenespiro[3.4]octane is 1.025 +/- 0.027.