dimethyl 3-phenylcyclopentane-1,1-dicarboxylate | 115340-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 3-phenylcyclopentane-1,1-dicarboxylate
• 英文别名: Dimethyl 3-phenyl-1,1-cyclopentanedicarboxylate
• CAS: 115340-08-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: JYDQKXIYPJYQSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 3-phenylcyclopentane-1,1-dicarboxylate 在 氢氧化钾 、 sodium hydroxide 、 甲烷磺酸 、 偶氮二异丁腈 、 碘苯二乙酸 、 碘 、 phosphorus pentoxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 76.0h， 生成 1,2,3,4-tetrahydro-1,4-methanonaphthalene-1-carboxylic acid
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p
• 作为产物：
  描述：

  4-Phenyl-2-methoxycarbonyl-4-enoic acid methyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丁酮 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 24.0h， 生成 dimethyl 3-phenylcyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  环状烯烃不对称氢化的手性杂碳环化合物

  摘要：

  通过使用环状烯烃的不对称氢化，已经合成了几种类型的手性杂环和碳环化合物。N，P连接的铱催化剂将具有各种取代基和杂官能团的六元环烯烃还原为良好至优异的对映选择性，而五元环烯烃的还原通常选择性较低，给出适度的对映异构体过量。氢化的立体选择性在很大程度上取决于五元环烯烃而不是六元环烯烃的底物结构。六元烯烃还原反应中形成的主要对映异构体可通过选择性模型预测，异构体烯烃具有互补的对映选择性，氢化后可得到相反的旋光异构体。顺式环己烷羧酸盐。

  DOI：

  10.1002/chem.201104073

文献信息

• Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl–Olefin Metathesis/Transfer Hydrogenation
  作者：Alexandre Djurovic、Marie Vayer、Zhilong Li、Regis Guillot、Jean-Pierre Baltaze、Vincent Gandon、Christophe Bour

  DOI：10.1021/acs.orglett.9b03240

  日期：2019.10.4

  catalytic tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation are described. 1,4-Cyclohexadiene has been used as an H2 surrogate to reduce the cyclic alkenes formed after the metathesis step. The same cationic gallium(III) complex, [IPr·GaCl2][SbF6], performs the two steps with functional group tolerance. This stereoselective reaction leads to 1,2-cis-disubstituted

  描述了催化串联过程的第一个例子，该过程涉及闭环羰基烯烃复分解和转移氢化。1,4-环己二烯已被用作H 2的替代品，以还原易位步骤后形成的环状烯烃。相同的阳离子镓（III）络合物[IPr·GaCl 2 ] [SbF 6 ]执行具有官能团耐受性的两个步骤。该立体选择性反应导致1，2-顺式-二取代的环戊烷和各种环己烷。DFT计算支持一种意想不到的机制，该机制涉及通过超亲电子的镓（III）二聚体活化1,4-环己二烯。
• Conformationally defined adrenergic agents. Part 13. Synthesis of benzobicyclo[3.2.1]octanes involving inversion of configuration via an N-to-O acetyl migration
  作者：Gary L. Grunewald、Qizhuang Ye

  DOI：10.1021/jo00252a026

  日期：1988.8
• GRUNEWALD, GARY L.;YE, QIZHUANG, J. ORG. CHEM., 53,(1988) N 17, 4021-4026
  作者：GRUNEWALD, GARY L.、YE, QIZHUANG

  DOI：——

  日期：——
• Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes
  作者：J. Johan Verendel、Jia-Qi Li、Xu Quan、Byron Peters、Taigang Zhou、Odd R. Gautun、Thavendran Govender、Pher G. Andersson

  DOI：10.1002/chem.201104073

  日期：2012.5.21

  Several types of chiral hetero‐ and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P‐Ligated iridium catalysts reduced six‐membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five‐membered cyclic alkenes was generally less selective, giving modest enantiomeric

  通过使用环状烯烃的不对称氢化，已经合成了几种类型的手性杂环和碳环化合物。N，P连接的铱催化剂将具有各种取代基和杂官能团的六元环烯烃还原为良好至优异的对映选择性，而五元环烯烃的还原通常选择性较低，给出适度的对映异构体过量。氢化的立体选择性在很大程度上取决于五元环烯烃而不是六元环烯烃的底物结构。六元烯烃还原反应中形成的主要对映异构体可通过选择性模型预测，异构体烯烃具有互补的对映选择性，氢化后可得到相反的旋光异构体。顺式环己烷羧酸盐。
• Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors
  作者：Robert M. Moriarty、Livia A. Enache、Lei Zhao、Richard Gilardi、Mariena V. Mattson、Om Prakash

  DOI：10.1021/jm970059p

  日期：1998.2.1

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.