methyl (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate | 70897-16-4

• 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: methyl (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate
• 英文别名: methyl (2R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate；(R)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid methyl ester；(R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester；6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid methyl ester；(R)-(+)-6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester；(R)-(+)-methyl 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate；methyl (2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylate
• CAS: 70897-16-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: WDQRGVNLHQEIOT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate 在 sodium hydroxide 、 sodium dithionite 、 三氯化铁 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 64.92h， 生成 (S)-(-)-methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate
  参考文献：
  名称：

  Studies on the total synthesis of (2R, 4'R, 8'R)-.alpha.-tocopherol (vitamin E). Stereospecific cyclizations leading to optically active chromans

  摘要：

  DOI：

  10.1021/jo00325a004
• 作为产物：
  描述：

  (R)-4-(2,5-Dihydroxy-3,4,6-trimethyl-phenyl)-2-hydroxy-2-methyl-butyric acid methyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.75h， 生成 methyl (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate
  参考文献：
  名称：

  Studies on the total synthesis of (2R, 4'R, 8'R)-.alpha.-tocopherol (vitamin E). Stereospecific cyclizations leading to optically active chromans

  摘要：

  DOI：

  10.1021/jo00325a004

文献信息

• Synthesis and screening of novel vitamin E derivatives for anticancer functions
  作者：Wenbin Chen、Sook Kyung Park、Weiping Yu、Ailian Xiong、Bob G. Sanders、Kimberly Kline

  DOI：10.1016/j.ejmech.2012.09.045

  日期：2012.12

  RRR-α-tocopherol to synthesize 6 vitamin E derivatives, and evaluated the anticancer actions in vitro for ability to induce cell death by apoptosis of human MCF-7 and MDA-MB-231 breast cancer cell lines and mouse mammary cancer cell line 66cl-4GFP. All derivatives, with the exception of compound 12, exhibited anticancer properties. The modified α-TEA ether-type phytyl group exhibited the highest pro-apoptotic

  α-TEA，RRR-α生育酚醚连接乙酸，表现出强效的抗癌作用的体外和体内; 然而，母体分子没有抗癌活性。在这项研究中，我们在色头和α-TEA以及RRR-α生育酚的植基尾部之间的色头和/或醚键PJ内置氟合成6个维生素E衍生物，并评价了抗癌作用在体外对能够通过人MCF-7和MDA-MB-231乳腺癌细胞系和小鼠乳腺癌细胞系66cl-4GFP的凋亡诱导细胞死亡。所有衍生物，化合物12除外，表现出抗癌特性。与α-TEA和其他维生素E衍生物相比，修饰的α-TEA醚型植酸基具有最高的促凋亡活性。
• 3,4-dihydro-2H-1-benzopyran derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04785017A1

  公开（公告）日：1988-11-15

  The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2 is hydrogen or halogen; R.sup.3, R.sup.4 and R.sup.5 are hydrogen, acyl or lower alkyl; R.sup.6 and R.sup.7, independently, are hydrogen or lower alkyl; X is alkylene.sub.3-7 ; and n is an integer of zero to four; provided that only one of R.sup.3, R.sup.4 or R.sup.5 can be acyl; enantiomers thereof, and, when R.sup.7 is hydrogen, salts thereof with pharmaceutically acceptable bases. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions.

  该发明涉及以下结构的化合物 ##STR1## 其中R.sup.1是氢或低碳基；R.sup.2是氢或卤素；R.sup.3、R.sup.4和R.sup.5是氢、酰基或低碳基；R.sup.6和R.sup.7独立地是氢或低碳基；X是烷基亚3-7；n是0到4的整数；但R.sup.3、R.sup.4或R.sup.5中只有一个可以是酰基；其对映体；当R.sup.7为氢时，其与药用可接受的碱形成的盐。公式I和II的化合物可用作治疗过敏症的药物。
• 3,6-Dioxo-1,4-cyclohexadien-1-yl-butandate esters
  申请人：Hoffmann-La Roche Inc.

  公开号：US04150050A1

  公开（公告）日：1979-04-17

  A process for inversion of the stereo configuration of (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetraalkyl-2H-1-benzopyran-2-carboxy lic acid and derivatives thereof to form the corresponding S-(-) acid and intermediates in this process.

  将(R)-(+)-3,4-二氢-6-羟基-2,5,7,8-四烷基-2H-1-苯并吡喃-2-羧酸及其衍生物的立体构型反转的过程，形成相应的S-(-)酸和该过程中的中间体。
• Chemical compound containing a superoxide scavenger and an organic nitrate or nitrite moiety
  申请人：Teijin Limited

  公开号：US06346634B1

  公开（公告）日：2002-02-12

  Compounds for use in the treatment of heart disease include a superoxide scavenger and an organic nitrate or nitrite moiety. The compounds can be represented by the formula (A)n(B)m, in which A is a superoxide scavenger, B is an organic nitrate or organic nitrite moiety, and n and m are values between 1 and 8. These compounds do not suffer from the problem of patient tolerance that is associated with the use of conventional agents such as organic nitrates.

  用于治疗心脏疾病的化合物包括超氧化物清除剂和有机硝酸酯或硝酸盐基团。这些化合物可以用公式(A)n(B)m表示，其中A是超氧化物清除剂，B是有机硝酸酯或有机硝酸盐基团，n和m的值在1和8之间。这些化合物不会出现与使用传统药物如有机硝酸酯相关的患者耐受性问题。
• Inversion process
  申请人：Hoffmann-La Roche Inc.

  公开号：US04205001A1

  公开（公告）日：1980-05-27

  A process for inversion of the stereo configuration of (R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetraalkyl-2H-1-benzopyran-2-carboxy lic acid and derivatives thereof to form the corresponding S-(-) acid and intermediates in this process.

  一种用于将(R)-(+)-3,4-二氢-6-羟基-2,5,7,8-四烷基-2H-1-苯并吡喃-2-羧酸及其衍生物的立体构型反转为相应的S-(-)酸的过程，以及这个过程中的中间体。