3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene | 144150-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene
• 英文别名: estra-1,3,5(10)-triene-3,17-diyl toluene-p-sulfonate；Estra-1,3,5(10)-trien-3,17β-diyl di-p-toluolsulfonat；3,17β-bis-(toluene-4-sulfonyloxy)-estra-1,3,5(10)-triene；3,17β-Bis-(toluol-4-sulfonyloxy)-oestra-1,3,5(10)-trien；[(8R,9S,13S,14S,17S)-13-methyl-3-(4-methylphenyl)sulfonyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 4-methylbenzenesulfonate
• CAS: 144150-78-7
• 化学式: C₃₂H₃₆O₆S₂
• 分子量: 580.766
• InChiKey: BBWQCARNGSDBOO-KQLGDFJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 144.0h， 生成 17α-amino-1,3,5(10)-estratrien-3-ol
  参考文献：
  名称：

  A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis

  摘要：

  The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00063-4
• 作为产物：
  描述：

  雌二醇 、 对甲苯磺酰氯 在 吡啶 作用下， 以87%的产率得到3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene
  参考文献：
  名称：

  A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis

  摘要：

  The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00063-4

文献信息

• Cross-Coupling of Phenol Derivatives with Umpolung Aldehydes Catalyzed by Nickel
  作者：Leiyang Lv、Dianhu Zhu、Jianting Tang、Zihang Qiu、Chen-Chen Li、Jian Gao、Chao-Jun Li

  DOI：10.1021/acscatal.8b01224

  日期：2018.5.4

  cross-coupling to construct the C(sp2)–C(sp3) bond was developed from two sustainable biomass-based feedstocks: phenol derivatives with umpolung aldehydes. This strategy features the in situ generation of moisture/air-stable hydrazones from naturally abundant aldehydes, which act as alkyl nucleophiles under catalysis to couple with readily available phenol derivatives. The avoidance of using both halides

  镍催化交叉偶联以构建C（sp 2）–C（sp 3）债券是从两种可持续的以生物质为基础的原料开发出来的：苯酚衍生物和戊醛。该策略的特征是由天然丰富的醛原位生成水分/空气不稳定的azo，这些醛在催化下可与烷基亲核试剂偶联，并与易得的苯酚衍生物偶联。避免同时使用卤化物作为亲电子试剂和避免使用有机金属或有机硼试剂（也衍生自卤化物）作为亲核试剂使该方法更具可持续性。耐水性，强大的官能团（酮，酯，游离胺，酰胺等）的相容性，以及复杂生物分子的后期精制，证明了其与有机金属试剂相比具有实用性和独特的化学选择性。
• Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates
  作者：On Ying Yuen、Xiangmeng Chen、Junyu Wu、Chau Ming So

  DOI：10.1002/ejoc.202000176

  日期：2020.3.31

  The first general palladium‐catalyzed α‐arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. The catalyst system comprising of Pd(OAc)2 and XPhos is highly effective towards this reaction. A wide range of aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles smoothly and catalyst loadings as low as 0.1 mol‐% Pd can be achieved.

  据报道，第一个普通的钯催化的芳基乙腈与芳基和杂芳基磺酸盐的α-芳基化反应。由Pd（OAc）2和XPhos组成的催化剂体系对该反应非常有效。各种各样的芳基/杂芳基甲苯磺酸酯和甲磺酸酯与芳基乙腈平滑地偶联，催化剂负载量可低至0.1 mol％Pd。
• Wang, Feng; Chiba, Kazuhiro; Tada, Masahiro, Journal of the Chemical Society. Perkin transactions I, 1992, # 15, p. 1897 - 1900
  作者：Wang, Feng、Chiba, Kazuhiro、Tada, Masahiro

  DOI：——

  日期：——
• Synthese und Antitumoraktivität voncis-Dichloroplatin(II)-Komplexen mit Östradiolderivaten
  作者：Henri Brunner、Gerhard Sperl

  DOI：10.1007/bf00808513

  日期：1993.1

  Estrogen-receptor binding moieties were introduced into Pt(II) complexes in order to facilitate the selective transport into cancer cells. Estradiol esters of 2,3-diaminopropionic acid and estradiol ethers of 1,2-diamino-2-methyl-3-(p-hydroxyphenyl)propane were attached to Pt(II) complexes. The antitumor activity of the compounds was tested towards the human mammary carcinoma cell lines MDA-MB 231 and MCF-7, respectively, and the estrogen-receptor binding affinity of the Pt(II) complexes was determined. The steroidal Pt(II) complexes gave a maximum growth inhibition of 80% and a maximum estrogen-receptor binding affinity of 5.18.
• Method of preparing alpha-estradiol
  申请人：LAB FRANCAIS CHIMIOTHERAPIE

  公开号：US02835681A1

  公开（公告）日：1958-05-20