<1S^*,2S^*,(S)R^*>-2-(phenylsulfinyl)cyclohexanol | 125074-83-1

• 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: <1S^*,2S^*,(S)R^*>-2-(phenylsulfinyl)cyclohexanol
• 英文别名: (1R,2R)-2-[(S)-phenylsulfinyl]cyclohexan-1-ol
• CAS: 125074-83-1
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: DSTRCQKAHARNSH-LALPHHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  <2S^*,(S)R^*>-2-(phenylsulfinyl)cyclohexanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到<1S^*,2S^*,(S)R^*>-2-(phenylsulfinyl)cyclohexanol
  参考文献：
  名称：

  Stereoselective reductions of 2-keto sulfoxides with hydrides

  摘要：

  DOI：

  10.1021/jo00294a027

文献信息

• Diastereoselective Synthesis of -Hydroxy Sulfoxides: Enzymatic and Biomimetic Approaches
  作者：Stefano Colonna、Vincenza Pironti、Francesca Zambianchi、Gianluca Ottolina、Nicoletta Gaggero、Giuseppe Celentano

  DOI：10.1002/ejoc.200600624

  日期：2007.1

  Stereoselectivities of up to 98 % have been found in the enzymatic synthesis of β-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase (CHMO). The diastereoselectivity of the “one-pot” preparation of the title compounds in the presence of bovine serum albumin has also been investigated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  在由环己酮单加氧酶 (CHMO) 催化的 β-羟基亚砜的酶促合成中，已发现立体选择性高达 98%。还研究了在牛血清白蛋白存在下“一锅”制备标题化合物的非对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Fluoro alcohol as reaction medium: one-pot synthesis of β-hydroxy sulfoxides from epoxides
  作者：Venkitasamy Kesavan、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1016/s0040-4039(00)00305-1

  日期：2000.4

  β-Hydroxy sulfoxides were obtained in one-pot synthesis by the ring opening of oxiranes with thiols in hexafluoroisopropanol (HFIP) without any catalyst, followed by in situ oxidation under neutral conditions. The reaction is anti-selective. β-Hydroxy sulfoxides were transformed by pyrolysis in the corresponding allylic alcohols.

  通过一锅法合成β-羟基亚砜，方法是在没有任何催化剂的情况下，在六氟异丙醇（HFIP）中将氧杂环戊烷与硫醇开环，然后在中性条件下原位氧化。该反应是反选择性的。通过在相应的烯丙基醇中热解来转化β-羟基亚砜。
• Stereoselective hydride reductions of chiral 2-p-tolylsulfinylcycloalkanones
  作者：Ana B. Bueno、M. Carmen Carreño、Jose L. García Ruano、Begoña Peña、Almudena Rubio、Miguel A. Hoyos

  DOI：10.1016/s0040-4020(01)85512-5

  日期：——

  The highly stereoselective hydride reductions of chiral 2-p-tolylsulfinyl-cyclopentanones and cycloheptanones are described. With DIBAL (electrophilic hydride) the configuration induced at C-1 is controlled by the sulfinyl group (1,3-asymmetric induction), and it can be inverted by using ZnCl2 as catalyst. With L-selectride the stereoselectivity is directed by the C-2 chiral groups (1,2-asymmetric induction). Other nucleophilic hydrides gave results which depend on the reagents and the size of the rings.