cis-(2R,3R)-t-butyl 3-phenyltetrahydrofuran-2-carboxylate | 345949-81-7

• 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: cis-(2R,3R)-t-butyl 3-phenyltetrahydrofuran-2-carboxylate
• 英文别名: (2R,3R)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate；t-butyl (2R,3R)-3-phenyltetrahydrofuran-2-carboxylate；tert-butyl (2R,3R)-3-phenyloxolane-2-carboxylate
• CAS: 345949-81-7
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: ZLYLTSAQZSVGPA-CHWSQXEVSA-N

物化性质

• 沸点：
  331.1±30.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-(2R,3R)-t-butyl 3-phenyltetrahydrofuran-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 生成 ((2R,3R)-3-Phenyl-tetrahydro-furan-2-yl)-methanol
  参考文献：
  名称：

  Co（III）-salen催化的类胡萝卜素反应：衍生自烯丙基芳基硫醚的S-ylides的立体选择性[2,3]σ重排

  摘要：

  烯丙基芳基硫醚和重氮乙酸酯在光学活性的Co（III）-salen配合物（4）的存在下以良好的对映选择性反应，得到[2,3]σ重排产物2-芳硫基-3-芳基-4-戊烯酸酯，通过相应的S-烷基。

  DOI：

  10.1016/s0040-4039(97)00639-4
• 作为产物：
  描述：

  (R)-(+)-3-氯-1-苯基-1-丙醇 在 (+)-(R,R)-bis[(Me₅C₅)Fe(C₄H₃N)]CH₂ potassium hydride 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 21.5h， 生成 cis-(2R,3R)-t-butyl 3-phenyltetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Applications of planar-chiral heterocycles in enantioselective catalysis: Cu(I)/bisazaferrocene-catalyzed asymmetric ring expansion of oxetanes to tetrahydrofurans

  摘要：

  A planar-chiral. C-2-symmetric bisazaferrocene ligand is shown to control the stereochemistry of Cu(I)-catalyzed ring expansions of oxetanes to tetrahydrofurans (C) 2001 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00082-5

文献信息

• Asymmetric Carbene C–O Insertion Reaction Using Optically Active Bipyridine-Copper Complex as a Catalyst. Ring Expansion of Oxetanes to Tetrahydrofurans
  作者：Katsuji Ito、Tsutomu Katsuki

  DOI：10.1246/cl.1994.1857

  日期：1994.10

  Copper complex of (7R,7R′)-7,7′-di(1-t-butyldimethylsiloxy-1-methylethyl)-6,6′,7,7′-tetrahydro-5H,5′H-2,2′-bi-1,1′-pyrindine (3) was found to be an effective catalyst for asymmetric carbene insertion reaction into the C-O bond of oxetanes. For example, the reaction of dl-2-phenyloxetane and t-butyl diazoacetate in the presence of Cu-3 complex provided trans- and cis-t-butyl 3-phenyltetrahydrofuran-2-carboxylate of 75% ee and 81% ee, respectively.

  (7R,7R′)-7,7′-二(1-t-丁基二甲基硅氧基-1-甲基乙基)-6,6′,7,7′-四氢-5H,5′H-2,2′-双-1,1′-吡啶铜复合物（3）被发现是一种有效的催化剂，用于不对称氮气插入反应进入氧杂环的C-O键。例如，dl-2-苯氧杂环与t-丁基二硝基乙酸酯在Cu-3复合物存在下的反应，分别提供了75%和81%对映体过剩的反-和顺- t-丁基 3-苯基四氢呋喃-2-羧酸酯。
• Enantiopsecific Ring Expansion of Oxetanes: Stereoselective Synthesis of Tetrahydrofurans
  作者：Tsutomu Katsuki、Katsuji Ito、Miwa Yoshitake

  DOI：10.3987/com-95-s35

  日期：——

  Enantiospecific ring expansion of oxetanes to tetrahydrofurans with diazoacetic acid ester was found to be catalyzed by the copper complex of (7R,7'R)-7,7'-di(1-tert-butyldimethylsiloxy-1-methylethyl)-6,6',7,7'-tetrahydro-5H,5'H-2,2'-bi-1,1'-pyrindine (4). For example, the reaction of (R)-2-phenyloxetane of 89% ee and tert-buryl diazoacetate with Cu-4 complex as a catalyst provided (2S,3R)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 92% ee as a major product, while that of (S)-2-phenyloxetane of 85% ee provided (2S,3S)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 93% ee as a major one.
• Applications of planar-chiral heterocycles in enantioselective catalysis: Cu(I)/bisazaferrocene-catalyzed asymmetric ring expansion of oxetanes to tetrahydrofurans
  作者：Michael M.-C. Lo、Gregory C. Fu

  DOI：10.1016/s0040-4020(01)00082-5

  日期：2001.3

  A planar-chiral. C-2-symmetric bisazaferrocene ligand is shown to control the stereochemistry of Cu(I)-catalyzed ring expansions of oxetanes to tetrahydrofurans (C) 2001 Elsevier Science Ltd, All rights reserved.
• Co(III)-salen catalyzed carbenoid reaction: Stereoselective [2,3]sigmatropic rearrangement of S-ylides derived from allyl aryl sulfides
  作者：Tsutomu Fukuda、Tsutomu Katsuki

  DOI：10.1016/s0040-4039(97)00639-4

  日期：1997.5

  Allyl aryl sulfides and diazoacetic acid esters react in the presence of optically active Co(III)-salen complex (4) with good enantioselectivity, to give the [2,3]sigmatropic rearrangement products, 2-arylthio-3-aryl-4-pentenoic acid esters, via the corresponding S-ylides.

  烯丙基芳基硫醚和重氮乙酸酯在光学活性的Co（III）-salen配合物（4）的存在下以良好的对映选择性反应，得到[2,3]σ重排产物2-芳硫基-3-芳基-4-戊烯酸酯，通过相应的S-烷基。