(-)-(3R,4S)-6-cyano-3,4-dihydroxy-2,2-dimethylchromane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (-)-(3R,4S)-6-cyano-3,4-dihydroxy-2,2-dimethylchromane
• 英文别名: (+)-trans-3,4-Dihydroxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile；(3R,4S)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: FQUMZEVXUBFFLN-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4S)-6-cyano-3,4-dihydroxy-2,2-dimethylchromane 生成 (3S,4R)-trans-3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile
  参考文献：
  名称：

  Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

  摘要：

  The chiral intermediate diol (3S,4R)-trans-3,4-dihydro-3,4-dihydroxydimethyl-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 2 was prepared for the total synthesis of a potassium channel opener drug candidate. The stereoselective acetylation of racemic 1 was carried out with various lipases among which the lipases from Candida cylindraceae and Pseudomonas cepacia catalyzed the acetylation of the undesired enantiomer of racemic 1 to yield monoacetylated product and unreacted desired (+)-trans diol 2. A reaction yield of >40% and an optical purity >90% were obtained using each lipase.

  DOI：

  10.1016/0957-4166(94)00367-k
• 作为产物：
  描述：

  (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到(-)-(3R,4S)-6-cyano-3,4-dihydroxy-2,2-dimethylchromane
  参考文献：
  名称：

  Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

  摘要：

  The chiral intermediate diol (3S,4R)-trans-3,4-dihydro-3,4-dihydroxydimethyl-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 2 was prepared for the total synthesis of a potassium channel opener drug candidate. The stereoselective acetylation of racemic 1 was carried out with various lipases among which the lipases from Candida cylindraceae and Pseudomonas cepacia catalyzed the acetylation of the undesired enantiomer of racemic 1 to yield monoacetylated product and unreacted desired (+)-trans diol 2. A reaction yield of >40% and an optical purity >90% were obtained using each lipase.

  DOI：

  10.1016/0957-4166(94)00367-k

文献信息

• Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin
  作者：Philip C. Bulman Page、Yohan Chan、Abu Hassan Noor Armylisas、Mohammed Alahmdi

  DOI：10.1016/j.tet.2016.10.070

  日期：2016.12

  Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.

  亚胺盐催化剂在非水条件下介导的色酮的有机催化不对称环氧化提供了高达99％的ee。相反，在水性条件下的反应可以形成相应的二醇产物，其ee s高达71％。该方法已用于合成东非药用植物代谢产物（3 S，4 R）-反式-3,4-二羟基-3,4-二氢软糖。
• Enzymatic preparation of chiral epoxide or hydroxy compounds by stereoselective epoxidation or hydroxylation
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0629702A2

  公开（公告）日：1994-12-21

  An enzymatic process for the preparation of chiral epoxides, monohydroxy or dihydroxy compounds of formula by the stereoselective epoxidation or hydroxylation of benzopyrans of formula or resolution of compounds of formula The compounds of formula I and II are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.

  一种通过式苯并吡喃的立体选择性环氧化或羟基化反应制备式手性环氧化物、单羟基或二羟基化合物的酶法工艺 通过式苯并吡喃的立体选择性环氧化或羟基化 或式化合物的解析 式 I 和 II 化合物是用于制备吡喃基氰基胍衍生物的中间体。
• An unusual base-mediated ring contraction reaction of benzopyrans to benzofurans
  作者：Derek R. Buckle、Andrew Faller、Ivan L. Pinto、David G. Smith

  DOI：10.1016/s0040-4039(00)91873-2

  日期：1992.2

  The reaction of electron deficient pyrroles and pyrazoles with trans 3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol under basic conditions results in the formation of 2-isopropylbenzofurans by a mechanism which appears to be dependent on the rate of the competitive dehydration reaction leading to the corresponding benzopyrans.
• US5478734A
  申请人：——

  公开号：US5478734A

  公开（公告）日：1995-12-26
• Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile
  作者：Ramesh N. Patel、Amit Banerjee、Clyde G. McNamee、Laszlo J. Szarka

  DOI：10.1016/0957-4166(94)00367-k

  日期：1995.1

  The chiral intermediate diol (3S,4R)-trans-3,4-dihydro-3,4-dihydroxydimethyl-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 2 was prepared for the total synthesis of a potassium channel opener drug candidate. The stereoselective acetylation of racemic 1 was carried out with various lipases among which the lipases from Candida cylindraceae and Pseudomonas cepacia catalyzed the acetylation of the undesired enantiomer of racemic 1 to yield monoacetylated product and unreacted desired (+)-trans diol 2. A reaction yield of >40% and an optical purity >90% were obtained using each lipase.