(+)-dihydrocompactin | 78366-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+)-dihydrocompactin
• 英文别名: [(1S,4aR,7S,8S,8aS)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• CAS: 78366-44-6
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: VXDSGTRNDFHIJB-CGDGMRKMSA-N

物化性质

• 熔点：
  144-145 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2); ethyl ether (60-29-7))
• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-dihydrocompactin 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以7.5 mg的产率得到4a-α-tetrahydrocompactin
  参考文献：
  名称：

  New Decalin Derivatives, Eujavanoic Acids A and B, from Eupenicillium javanicum

  摘要：

  Two new decalin derivatives, eujavanoic acids A (1) and B (2), were isolated from Eupenicillium javanicum, along with several compactin derivatives. The structures of 1 and 2 were determined by spectroscopic methods and modified Mosher's method. The side chain (2-methylbutanoyloxy) and acid functionalities of compactin derivatives were necessary to show the antifungal activity.

  DOI：

  10.1021/np040052s
• 作为产物：
  描述：

  methyl (1R*,2S*,4R*,4aS*,8R*,8aS*)-8-(tert-butyldimethylsiloxy)-4-hydroxy-2-methyldecahydronaphthalene-1-carboxylate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 二乙基甲氧基硼烷 、 氢氟酸 、 四丁基氟化铵 、 四氯化钛 、 sodium hydride 、 potassium carbonate 、 magnesium 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.08h， 生成 (+)-dihydrocompactin
  参考文献：
  名称：

  Total synthesis of (+)-dihydrocompactin

  摘要：

  The total synthesis of (+)-dihydrocompactin 1 has been achieved by employing double Michael reaction of 3-(tert-butyldimethylsiloxy)-1-acetylcyclohexene 13 with methyl crotonate and the TiCl4-promoted aldol condensation of the bis(trimethylsilyl enol ether) of methyl acetoacetate 7 as key reactions.

  DOI：

  10.1039/p19940002417

文献信息

• Remote Asymmetric Induction in an Intramolecular Ionic Diels−Alder Reaction:  Application to the Total Synthesis of (+)-Dihydrocompactin
  作者：Tarek Sammakia、Deidre M. Johns、Ganghyeok Kim、Martin A. Berliner

  DOI：10.1021/ja043506g

  日期：2005.5.1

  The total synthesis of (+)-dihydrocompactin via an intramolecular ionic Diels-Alder reaction that proceeds with remote stereocontrol is described. This reaction proceeds by an intermediate vinyl-oxocarbenium ion (6), the conformational constraints of which lead to the observed asymmetric induction. The sense of asymmetric induction appears contrasteric and is explained by the proposed reactive conformation

  描述了 (+)-dihydrocompactin 通过分子内离子 Diels-Alder 反应进行远程立体控制的全合成。该反应通过中间体乙烯基氧碳鎓离子 (6) 进行，其构象限制导致观察到的不对称诱导。不对称感应的感觉是对比的，并且可以通过图 1 中所示的拟议反应构象来解释。
• Synthesis of (+)-dihydrocompactin and (+)-compactin via vinylsilane terminated cationic cyclization
  作者：Steven D. Burke、David N. Deaton

  DOI：10.1016/s0040-4039(00)92272-x

  日期：1991.1

  described, featuring cationic polyene cyclization mediated by a vinylsilane terminating group and a benzenedimethanol acetal initiator. Further transformations resulting in formal and total syntheses of (+)-compactin and (+)-dihydrocompactin, respectively, are also reported.

  描述了对八醇二醇1的两种对映选择性路线，其特征在于由乙烯基硅烷末端基团和苯二甲醇缩醛引发剂介导的阳离子多烯环化。还报道了进一步的转化，分别导致（+）-compactin和（+）-dihydrocompactin的形式和全部合成。
• Total synthesis of (+)-dihydrocompactin
  作者：Hisahiro Hagiwara、Masakazu Kon-no、Hisashi Uda

  DOI：10.1039/c39920000866

  日期：——

  The total synthesis of (+)-dihydrocompactin 1 has been achieved by employing the double Michael reaction of 3-tert-butyldimethylsilyloxy-1-acetylcyclohexene with methyl crotonate as a key step.

  已通过采用3-叔丁基二甲基硅氧基-1-乙酰基环己烯与甲基巴豆酸酯的双迈克尔反应作为关键步骤，实现了(+)-二氢紧凑菌素1的全合成。
• New Decalin Derivatives, Eujavanoic Acids A and B, from <i>Eupenicillium </i><i>j</i><i>avanicum</i>
  作者：Shigeru Okamoto、Tomoo Hosoe、Takeshi Itabashi、Koohei Nozawa、Kaoru Okada、Galba Maria de Campos Takaki、Minoru Chikamori、Takashi Yaguchi、Kazutaka Fukushima、Makoto Miyaji、Ken-ichi Kawai

  DOI：10.1021/np040052s

  日期：2004.9.1

  Two new decalin derivatives, eujavanoic acids A (1) and B (2), were isolated from Eupenicillium javanicum, along with several compactin derivatives. The structures of 1 and 2 were determined by spectroscopic methods and modified Mosher's method. The side chain (2-methylbutanoyloxy) and acid functionalities of compactin derivatives were necessary to show the antifungal activity.