rac-cis-3-(1,1-ethylenedioxyethyl)-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-1,3-diol | 76155-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: rac-cis-3-(1,1-ethylenedioxyethyl)-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-1,3-diol
• 英文别名: (1R,3R)-5,8-dimethoxy-3-(2-methyl-1,3-dioxolan-2-yl)-2,4-dihydro-1H-naphthalene-1,3-diol
• CAS: 76155-88-9
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: OEYVXRGDZFMFLZ-BDJLRTHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rac-cis-3-(1,1-ethylenedioxyethyl)-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-1,3-diol 生成 rac-cis-3-(1,1-ethylenedioxyethyl)-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-1,3-diol
  参考文献：
  名称：

  BROADHURST, M. J.;HASSALL, C. H.;THOMAS, G. J.

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,9R)-3,6-dimethoxy-9-(2-methyl-1,3-dioxolan-2-yl)-11-phenyl-10,12-dioxa-11-boratricyclo[7.3.1.02,7]trideca-2,4,6-triene 生成 rac-cis-3-(1,1-ethylenedioxyethyl)-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-1,3-diol
  参考文献：
  名称：

  BROADHURST, M. J.;HASSALL, C. H.;THOMAS, G. J.

  摘要：

  DOI：

文献信息

• Cyclic compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US04302398A1

  公开（公告）日：1981-11-24

  The present invention relates to naphthacene derivatives. More particularly, the invention is concerned with a process for the manufacture of hexahydronaphthacene derivatives and with certain of said derivatives per se. The invention is also concerned with novel intermediates occurring in said process and with the preparation thereof. There are presented hexahydronaphthacene derivatives of the formula ##STR1## wherein R.sup.1 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## , in which R.sup.2 and R.sup.3 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group, or --(CH.sub.2).sub.n --OY b in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group. Also presented are intermediates and a process to produce the compounds of formula I.

  本发明涉及萘酮衍生物。更具体地，该发明涉及一种用于制造六氢萘酮衍生物的方法，以及其中某些衍生物本身。该发明还涉及在该方法中出现的新型中间体以及其制备方法。提供了具有下述结构的六氢萘酮衍生物：其中R.sup.1代表较低的烷基或酯化羧基或具有下述结构的基团：其中R.sup.2和R.sup.3一起形成氧代基或受保护的氧代基，X代表氢原子或羟基或酰氧基，或--(CH.sub.2).sub.n--OY，其中n代表1或2，Y代表氢原子或烷基或酰基。还提供了中间体和生产式I化合物的方法。
• A convergent synthesis of (+)-4-demethoxydaunomycinone and ( + )-daunomycinone
  作者：John S. Swenton、John N. Freskos、Gary W. Morrow、Anthony D. Sercel

  DOI：10.1016/s0040-4020(01)91523-6

  日期：1984.1

  mercaptole).Two noteworthy aspects of the synthesis were the highly selective reduction of a bicyclic β-hydroxyketone to afford a diol with the required cis-stereochemistry at the eventual C-7 and C-9 positions of the anthracyclinone and the regioselective hydrolysis of the quinone bisketal to afford the monoketal of proper regiochemistry for the synthesis of( + )-daunomycinone. Thus, ( + )-daunomycinone

  据报道，通过官能化的醌单缩酮与相应的3-氰基-1-（3H）异苯并呋喃酮的阴离子的缩合反应，可以合成（+）-4-脱甲氧基十二烷酮和（+）-十二烷酮。不用色谱法，由2，5-二甲氧基苯甲醛按十六步制备醌单缩酮序列。通过从（-）-α-甲基苄基胺和1,2,3,4，-四氢-5,8-二甲基4-（亚乙基硫醇）拆分亚胺获得适当绝对构型的单缩酮。合成是高选择性还原双环β-羟基酮，得到具有所需顺式的二醇蒽环素最终在C-7和C-9位置进行立体化学反应，以及醌双缩酮的区域选择性水解，从而为合成（+）-柔红霉素提供了适当的区域化学单酮。因此，以十九个步骤由2，5-二甲氧基苯甲醛以（分别为3和5％的总收率（外消旋材料的总收率为13％））制备了（+）-金牛烯酮和（+）-4-脱甲氧基金牛烯酮。这种合成策略允许对各种D环类似物采用收敛方法。
• Process for the preparation of hexahydronaphthacene derivatives
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0013577A2

  公开（公告）日：1980-07-23

  Cyclic compounds of the general formula wherein one of R' and R2 is hydrogen and the other is hydrogen or hydroxy or R' and R2 taken together are a protected oxo group; R3 is hydrogen, hydroxy or acyloxy; R' is lower alkyl, esterified carboxy or a group of the formula -C(R5, R6) -CH2-X; R' and R'taken together are oxo or protected oxo; X is hydrogen, hydroxy, acyloxy or -(CH2)n-OY; Y is hydrogen, alkyl or acyl and n is 1 or 2; with the proviso that one of R1 and R2 is hydrogen and the other is hydroxy or R1 and R2 taken together are protected oxo when R' is acetoxy and R' is acetyl; processes for the preparation thereof and intermediates in these processes.

  通式的环状化合物，其中R'和R2之一为氢，另一个为氢或羟基，或R'和R2合在一起为受保护的氧代基团；R3为氢、羟基或酰氧基；R'为低级烷基、酯化羧基或式-C(R5，R6)-CH2-X的基团；R'和R'合在一起为氧代或受保护的氧代；X为氢、羟基、酰氧基或-( )n-OY；Y为氢、烷基或酰基，n为1或2；但R1和R2之一为氢，另一个为羟基，或R1和R2合在一起为受保护的氧代，当R'为乙酰氧基，R'为乙酰基时；其制备工艺及其中间体。
• US4302398A
  申请人：——

  公开号：US4302398A

  公开（公告）日：1981-11-24
• US4316985A
  申请人：——

  公开号：US4316985A

  公开（公告）日：1982-02-23