(R)-(-)-2,2-diphenylcyclopentanol | 126421-67-8

• 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: (R)-(-)-2,2-diphenylcyclopentanol
• 英文别名: (1R)-2,2-diphenylcyclopentan-1-ol
• CAS: 126421-67-8
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: TYFASEURNPWTII-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2,2-diphenylcyclopentanol 在 potassium hydride 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2-((R)-2,2-Diphenylcyclopentoxy)ethanal
  参考文献：
  名称：

  Nitroalkene [4 + 2] Cycloadditions with 2-(Acyloxy)vinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-substituted-pyrrolidines

  摘要：

  2-(Acyloxy)vinyl ethers undergo regioselective [4 + 2] cycloadditions with nitroalkenes (promoted by SnCl4) to afford subsutituted 5-acetoxy nitronates in good yields (68-91%). Endo/exo selectivity in the cycloadditions has been found to be dependent on the nitroalkene substitution; 2-aryl-1-nitroalkenes provided exclusively exo cycloadducts while 2-cyclohexyl-1-nitroalkene 28 afforded predominately endo cycloadducts in a ratio of 12:1. The resulting nitronates can be elaborated to N-tosyl-4-substituted-3-hydroxypyrrolidines by hydrogenolysis (160 psi of H-2/PtO2) or to bicyclic alpha-hydroxy lactams by [3 + 2] cycloaddition followed by hydrogenation (14.7 psi of H-2/Raney nickel). A chiral 2-acetoxyvinyl ether derived from (R)-2,2-diphenylcyclopentanol has been employed in the cycloaddition-hydrogenation sequence to prepare an optically active N-tosyl-3-hydroxypyrrolidine in 96% ee.

  DOI：

  10.1021/jo00095a038
• 作为产物：
  描述：

  二苯乙腈 在 盐酸 、 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 116.83h， 生成 (R)-(-)-2,2-diphenylcyclopentanol
  参考文献：
  名称：

  (R)-(−)-2,2-DIPHENYLCYCLOPENTANOL

  摘要：

  DOI：

  10.15227/orgsyn.074.0033

文献信息

• New chiral auxiliaries: their use in the asymmetric hydrogenation of .beta.-acetamidocrotonates
  作者：Dominique Potin、Francoise Dumas、Jean D'Angelo

  DOI：10.1021/ja00165a036

  日期：1990.4

  Synthesis of chiral β-amido esters with high diastereoisomeric excess was achieved by asymmetric hydrogenation (H 2 /PtO 2 ) of stereogenic β-acetamidocrotonates in which the chirality is present in the alkyl of the ester part. For such a purpose, new efficient chiral auxiliaries such as 2,2-diphenylcyclopentanol and 1,1-diphenyl-3-methyl-2-butanol were developed

  通过不对称氢化 (H 2 /PtO 2 ) 立体异构 β-乙酰氨基巴豆酸酯（其中手性存在于酯部分的烷基中）来合成具有高非对映异构过量的手性 β-酰胺酯。为此，开发了新型高效手性助剂，如 2,2-二苯基环戊醇和 1,1-二苯基-3-甲基-2-丁醇
• Asymmetric induction in manganese(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetates and 2,5-dimethylpyrrolidine acetoacetamides
  作者：Qingwei Zhang、Raju M. Mohan、Laura Cook、Sophia Kazanis、Daniel Peisach、Bruce M. Foxman、Barry B. Snider

  DOI：10.1021/jo00079a006

  日期：1993.12

  Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90% of 13 with 86% de. Cyclization of 31b provided 56% of (+)-podocarpic acid precursor 32e with 82% de. The direction of de was opposite in these two cases. Oxidative cyclization of a-methyl beta-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while alpha-propyl beta-keto ester 44d produced a > 10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the alpha-substituent The reaction proceeds through transition states 12 and 56 with large alpha-substituents and through transition states 19 and 57 with small a-substituents. The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.
• Nitroalkene Inter [4 + 2]/Intra [3 + 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary
  作者：Scott E. Denmark、Mark E. Schnute、Lawrence R. Marcin、Atli Thorarensen

  DOI：10.1021/jo00115a042

  日期：1995.5

  Chiral enol ethers derived from (R)-(-)-2,2-diphenylcyclopentanol ((-)-3) have been found to provide high levels of asymmetric induction in tandem inter [4 + 2]/intra [3 + 2] nitroalkene cycloadditions. The chiral auxiliary (>97% ee) is readily prepared in three steps from diphenylacetonitrile employing an asymmetric oxazaborolidine-catalyzed borane reduction. Either enantiomeric series of tandem cycloaddition/hydrogenolysis product 7 is available from the chiral auxiliary of a single absolute configuration by judicious selection of the Lewis acid promoter, Ti(O-i-Pr)(2)Cl-2 (98% ee, (-)-7) or MAPh (93% ee, (+)-7). Propenyl ethers derived from (-)-3 undergo endo selective [4 + 2] cycloadditions (2.3/1 - 8.2/1) in the presence Ti(O-i-Pr)(2)Cl-2; however, exo selective [4 + 2] cycloadditions (10.2/1 - 54.8/1) are observed in the presence of MAPh.
• Enzymatic resolution of hindered secondary alcohols: Efficient access to a new simplified chiral auxiliary
  作者：Lalatiana R. Randrianasolo-Rakotozafy、Robert Azerad、Françoise Dumas、Dominique Potin、Jean d'Angelo

  DOI：10.1016/s0957-4166(00)80112-3

  日期：1993.5

  2,2-Diphenylcyclopentanol, an efficient chiral auxiliary which bears only one stereogenic center, as well as some related hindered secondary alcohols, were resolved by means of pig liver acetone powder (PLAP) and horse liver acetone powder (HLAP).
• Synthesis of (+)-Casuarine
  作者：Scott E. Denmark、Alexander R. Hurd

  DOI：10.1021/jo991680v

  日期：2000.5.1

  The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/ australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.