1,1-dimethoxy-1-(p-chlorophenyl)propane | 340020-33-9

• 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: 1,1-dimethoxy-1-(p-chlorophenyl)propane
• 英文别名: 1-Chloro-4-(1,1-dimethoxypropyl)benzene
• CAS: 340020-33-9
• 化学式: C₁₁H₁₅ClO₂
• 分子量: 214.692
• InChiKey: SLDUHIKTNKHUMO-UHFFFAOYSA-N

物化性质

• 沸点：
  243.9±25.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-1-(p-chlorophenyl)propane 在 ROMPgel lithium 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  ROMPgel-supported biphenyl and naphthalene: reagents for lithiation reactions with minimal purification

  摘要：

  The synthesis of ring opening metathesis, polymer (ROMPgel) supported naphthalene and biphenyl reagents was carried out. These reagents were utilized for catalytic lithiation reactions of aryl and alkyl chlorides and for the reductive deprotection of benzyl and allyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02317-6
• 作为产物：
  描述：

  甲醇 、 1-氯-4-(1-丙炔-1-基)苯 在 <(Cp*Ir)2(μ3-S)2PdCl2> 作用下， 反应 48.0h， 生成 1,1-dimethoxy-1-(p-chlorophenyl)propane 、 2,2-dimethoxy-1-(p-chlorophenyl)propane
  参考文献：
  名称：

  Regioselective Addition of Alcohols to Internal 1-Aryl-1-alkynes Catalyzed by a Triangular Heterobimetallic Ir₂Pd Sulfido Cluster

  摘要：

  研究发现，由[PdCl2(cod)]和[Cp*IrCl(μ-SH)2IrCp*Cl]制备的三角形杂多金属硫化物簇[(Cp*Ir)2(μ3-S)2PdCl2]能催化醇与炔的加成反应，生成相应的酮。特别是，内部 1-芳基-1-炔以高区域选择性转化为相应的 2,2-二烷氧基-1-芳基烷。事实证明，类似的 Ir2PtS2 簇的选择性要低得多。

  DOI：

  10.1246/cl.1998.717

文献信息

• Regioselective Addition of Alcohols to Internal 1-Aryl-1-alkynes Catalyzed by a Triangular Heterobimetallic Ir₂Pd Sulfido Cluster
  作者：Dai Masui、Youichi Ishii、Masanobu Hidai

  DOI：10.1246/cl.1998.717

  日期：1998.8

  The triangular heterobimetallic sulfido cluster[(Cp*Ir)2(μ3-S)2PdCl2] prepared from [PdCl2(cod)] and [Cp*IrCl(μ-SH)2IrCp*Cl] was found to catalyze the addition of alcohols to alkynes to give the corresponding ketals. In particular, internal 1-aryl-1-alkynes were transformed into the corresponding 2,2-dialkoxy-1-arylalkanes with high regioselectivity. The analogous Ir2PtS2 cluster proved to be much less selective.

  研究发现，由[PdCl2(cod)]和[Cp*IrCl(μ-SH)2IrCp*Cl]制备的三角形杂多金属硫化物簇[(Cp*Ir)2(μ3-S)2PdCl2]能催化醇与炔的加成反应，生成相应的酮。特别是，内部 1-芳基-1-炔以高区域选择性转化为相应的 2,2-二烷氧基-1-芳基烷。事实证明，类似的 Ir2PtS2 簇的选择性要低得多。
• Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships
  作者：Andrew Thurkauf、Mariena V. Mattson、Scott Richardson、Seid Mirsadeghi、Paul L. Ornstein、Ernest A. Harrison、Kenner C. Rice、Arthur E. Jacobson、James A. Monn

  DOI：10.1021/jm00086a001

  日期：1992.4

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.
• ROMPgel-supported biphenyl and naphthalene: reagents for lithiation reactions with minimal purification
  作者：Thomas Arnauld、Anthony G.M. Barrett、Brian T. Hopkins

  DOI：10.1016/s0040-4039(01)02317-6

  日期：2002.2

  The synthesis of ring opening metathesis, polymer (ROMPgel) supported naphthalene and biphenyl reagents was carried out. These reagents were utilized for catalytic lithiation reactions of aryl and alkyl chlorides and for the reductive deprotection of benzyl and allyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and structures of heterobimetallic Ir2M (MPd, Pt) sulfido clusters and their catalytic activity for regioselective addition of alcohols to internal 1-aryl-1-alkynes
  作者：Dai Masui、Takuya Kochi、Zhen Tang、Youichi Ishii、Yasushi Mizobe、Masanobu Hidai

  DOI：10.1016/s0022-328x(00)00619-7

  日期：2001.2

  The heterobimetallic trinuclear sulfido clusters [(Cp*Ir)(2)(mu (3)-S)(2)MCl2] (M = Pd (3), Pt (4); Cp* = eta (5)-C5Me5) were synthesized from the dinuclear hydrogensulfido complex [Cp*IrCl(mu -SH)(2)IrCp*Cl] (2) and [MCl2(COD)] (COD = cycloocta-1,5-diene), while the reaction of 2 with [Pd(PPh3)(4)] afforded the cationic trinuclear cluster [(Cp*Ir)(2)(mu (3)-S)(2)PdCl(PPh3)]Cl (5). Clusters 3 and 4 reacted with PPh3 to give a series of mono and dicationic clusters including 5, while the dicationic clusters [(Cp*Ir)(2)(mu (3)-S)(2)M(dppe)][BPh4](2) (M = Pd (9), Pt (10); dppe = Ph2PCH2CH2PPh2) were obtained by the reaction with dppe followed by anion metathesis. The molecular structures of 5 . CH2Cl2, 9 . CH3COCH3, and 10 . CH3COCH3 were determined by X-ray crystallography. Clusters 3 and 4 were found to catalyze the addition of alcohols to alkynes to give the corresponding acetals. Internal 1-aryl-1-alkynes were transformed by cluster 3 into the corresponding 2,2-dialkoxy-1-arylalkanes with high regioselectivity up to 99:1, while cluster 4 was a much less regioselective catalyst. (C) 2001 Elsevier Science B.V. All rights reserved.