(4S)-2,2-diphenyl-4-(hydroxymethyl)-1,3-dioxolane | 124918-09-8

• 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: (4S)-2,2-diphenyl-4-(hydroxymethyl)-1,3-dioxolane
• 英文别名: (S)-(2,2-diphenyl-[1,3]dioxolan-4-yl)methanol；[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]methanol；2,2-diphenyl-1,3-dioxolane-4-methanol
• CAS: 124918-09-8
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: WCYJCRIYOMOUOJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-2,2-diphenyl-4-(hydroxymethyl)-1,3-dioxolane 在 三乙胺 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 2.17h， 生成 (4S)-2,2-diphenyl-4-[(methylamino)methyl]-1,3-dioxolane
  参考文献：
  名称：

  Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships

  摘要：

  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.

  DOI：

  10.1021/jm00086a001
• 作为产物：
  描述：

  4-Chlormethyl-2,2-diphenyl-dioxolan 以 六甲基磷酰三胺 、 水 为溶剂， 反应 1.5h， 生成 (4S)-2,2-diphenyl-4-(hydroxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Enzymatic resolution of 2,2-disubstituted-1,3-dioxolane-4-methanol carboxylic esters

  摘要：

  The enantioselectivity of enzymatic hydrolysis of carboxylic esters of various 1,2-ketals of glycerol has been investigated. The influence of the ketal group has been studied. A number of lipases and proteinases have been tested and the best enantioselectivity was obtained with proteinase from Aspergillus oryzae which gave an E-value of 9 with 2,2-dimethyl-1,3-dioxolane-4-methanol butanoate. Variations in the acyl part revealed that butanoyl was optimal. All hydrolysis products have been synthesised in homochiral forms from homochiral starting materials.

  DOI：

  10.1016/s0957-4166(00)82313-7

文献信息

• Highly Enantioselective Intermolecular Hydroamination of Allylic Amines with Chiral Aldehydes as Tethering Catalysts
  作者：Melissa J. MacDonald、Colin R. Hesp、Derek J. Schipper、Marc Pesant、André M. Beauchemin

  DOI：10.1002/chem.201203462

  日期：2013.2.18

  Chirally LinkedIn: Chiral aldehydes are effective tethering catalysts for enantioselective intermolecular hydroamination, which provides access to vicinal diamine motifs in good yields and excellent enantioselectivities (see scheme). This work highlights simple chiral α‐oxygenated aldehydes as effective organocatalysts capable of efficiently inducing asymmetry through transient intramolecularity.

  手性醛：手性醛是对映选择性分子间加氢胺化的有效束缚催化剂，可提供高产率和优异对映选择性的邻位二胺基序（参见方案）。这项工作强调了简单的手性α-氧化醛作为有效的有机催化剂，能够通过瞬态分子内有效诱导不对称性。
• Effect of substituent on the enantioselectivity for lipase-catalyzed kinetic resolution of glycerol derivatives
  作者：Yasuhiro Kawanami、Akira Honnma、Kayo Ohta、Naoko Matsumoto

  DOI：10.1016/j.tet.2004.10.107

  日期：2005.1

  The lipase-catalyzed transesterifications of various substituted diphenyl 1,2-ketals of glycerol have been investigated. Efficient modification of the substrate structure with bis(4-bromophenyl) ketal was found to enhance the enantioselectivity up to E=57 at 0 °C.

  已经研究了甘油的各种取代的二苯基1，2-缩酮的脂肪酶催化的酯交换反应。发现使用双（4-溴苯基）缩酮有效修饰底物结构可在0°C时提高对映选择性至E = 57。
• Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline
  作者：Dai Terakado、Hitomi Koutaka、Takeshi Oriyama

  DOI：10.1016/j.tetasy.2005.01.034

  日期：2005.3

  A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline. (C) 2005 Elsevier Ltd. All rights reserved.
• Terao, Yoshiyasu; Tsuji, Keiichiro; Murata, Masakazu, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 6, p. 1653 - 1655
  作者：Terao, Yoshiyasu、Tsuji, Keiichiro、Murata, Masakazu、Achiwa, Kazuo、Nishio, Toshiyuki、et al.

  DOI：——

  日期：——