(4S)-4-(2-methyl-3-oxohept-6-en-2-yl)-2,2-dimethyl[1,3]dioxane | 305840-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-(2-methyl-3-oxohept-6-en-2-yl)-2,2-dimethyl[1,3]dioxane
• 英文别名: (S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylhept-6-en-3-one；(4S)-4-(2-Methyl-3-oxo-hept-6-en-2-yl)-2,2-dimethyl-[1,3] Dioxane；(4S)-4-(2-Methyl-3-oxo-hept-6-en-2-yl)-2,2-dimethyl-(1,3)dioxane；(4S)-4-(2-methyl-3-oxo-hept-6-en-2-yl)-2,2-dimethyl-[1,3]dioxane；(4S)-4-(2-methyl-3-oxo-hept-6-en-2-yl)-2,2-dimethyl-1,3-dioxane；(4S)-4-(2-methyl-3-oxohept-6-en-2-yl)-2,2-dimethyl-1,3-dioxane；2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-2-methylhept-6-en-3-one
• CAS: 305840-13-5
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: XUCKPVVDUREPQH-LBPRGKRZSA-N

物化性质

• 沸点：
  313.3±22.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-(2-methyl-3-oxohept-6-en-2-yl)-2,2-dimethyl[1,3]dioxane 在 2,6-二甲基吡啶 、 草酰氯 、 camphor-10-sulfonic acid 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (3S,6R,7S,8S,12Z,15S)-4,4,8,12-tetramethyl-5-oxo-6-allyl-3,7,15-tris-(tert-butyldimethylsilyloxy)-15-(2-methylbenzothiazol-5-yl)-pentadec-12-enal
  参考文献：
  名称：

  ZK-EPO的总合成和抗肿瘤活性：临床开发中的第一个完全合成的埃博霉素。

  摘要：

  DOI：

  10.1002/anie.200602785
• 作为产物：
  描述：

  (3RS,4S)-4-(2-methyl-3-hydroxy-hept-6-en-2-yl)-2,2-dimethyl-[1,3]dioxane 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 生成 (4S)-4-(2-methyl-3-oxohept-6-en-2-yl)-2,2-dimethyl[1,3]dioxane
  参考文献：
  名称：

  Efficient Chiral Pool Synthesis of the C1-C6 Fragment of Epothilones

  摘要：

  描述了一种从易得的手性原料(-)-泛内酯出发，高效合成紫杉醇C1-C6片段的手性池合成方法。

  DOI：

  10.1055/s-2004-834936

文献信息

• 6-Alkenyl-, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations
  申请人：Klar Ulrich

  公开号：US20050113429A1

  公开（公告）日：2005-05-26

  This invention describes the new 6-alkenyl- and 6-alkinyl-epothilone derivatives of general formula (I) in which R 1a , R 1b , R 2b , R 3a , R 3b , R 4 , R 5 , R 6 , R 7 , A, Y, D, E, G, Y and Z have the meanings that are indicated in the description. The new compounds interact with tubulin by stabilizing microtubuli that are formed. They are able to influence the cell-splitting in a phase-specific manner and thus find use in treating diseases or conditions associated with the need for cell growth, division and/or proliferation. Thus the compounds are suitable for treating malignant tumors, for example, ovarian, stomach, colon, adeno-, breast, lung, head and neck carcinomas, malignant melanoma, acute lymphocytic and myelocytic leukemia. In addition, they are suitable for anti-angiogenesis therapy as well as for treatment of chronic inflammatory diseases (such as psoriasis, arthritis). Methods of use and preparation of the compounds are also described.

  该发明描述了通式(I)中的新6-烯基-和6-炔基-epothilone衍生物，其中R1a、R1b、R2b、R3a、R3b、R4、R5、R6、R7、A、Y、D、E、G、Y和Z具有说明中指示的含义。这些新化合物通过稳定形成的微管蛋白质与微管结合。它们能够以特定阶段的方式影响细胞分裂，因此可用于治疗与细胞生长、分裂和/或增殖需求相关的疾病或状况。因此，这些化合物适用于治疗恶性肿瘤，例如卵巢、胃、结肠、腺癌、乳腺、肺、头颈癌、恶性黑色素瘤、急性淋巴细胞和骨髓性白血病。此外，它们也适用于抗血管生成治疗以及慢性炎症性疾病的治疗（如牛皮癣、关节炎）。还描述了这些化合物的使用方法和制备方法。
• 6-Alkenyl -, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations
  申请人：Klar Ulrich

  公开号：US20060046997A1

  公开（公告）日：2006-03-02

  This invention describes the new 6-alkenyl- and 6-alkinyl-epothilone derivatives of general formula (I) in which R 1a , R 1b , R 2a , R 3a , R 3b , R 4 , R 5 , R 6 , R 7 , A, Y, D, E, G, Y and Z have the meanings that are indicated in the description. The new compounds interact with tubulin by stabilizing microtubuli that are formed. They are able to influence the cell-splitting in a phase-specific manner and thus find use in treating diseases or conditions associated with the need for cell growth, division and/or proliferation. Thus the compounds are suitable for treating malignant tumors, for example, ovarian, stomach, colon, adeno-, breast, lung, head and neck carcinomas, malignant melanoma, acute lymphocytic and myelocytic leukemia. In addition, they are suitable for anti-angiogenesis therapy as well as for treatment of chronic inflammatory diseases (such as psoriasis, arthritis). Methods of use and preparation of the compounds are also described.

  该发明描述了新的6-烯基和6-炔基-依托酮衍生物，其一般式为（I），其中R1a、R1b、R2a、R3a、R3b、R4、R5、R6、R7、A、Y、D、E、G、Y和Z的含义如描述中所示。这些新化合物通过稳定形成的微管蛋白质与微管相互作用。它们能够以特定于阶段的方式影响细胞分裂，因此可用于治疗与细胞生长、分裂和/或增殖需求相关的疾病或症状。因此，这些化合物适用于治疗恶性肿瘤，例如卵巢、胃、结肠、腺癌、乳腺癌、肺癌、头颈癌、恶性黑色素瘤、急性淋巴细胞白血病和骨髓性白血病。此外，它们也适用于抗血管生成治疗以及慢性炎症性疾病（如牛皮癣、关节炎）的治疗。该文还描述了这些化合物的使用方法和制备方法。
• Protected 3,-5-dihydroxy-2,2-dimethyl-valeronitriles for the synthesis of epothilones and epothilone derivatives and process for the production
  申请人：Schering AG

  公开号：US20030149281A1

  公开（公告）日：2003-08-07

  The invention relates to 3,5-dihydroxy-2,2-dimethyl-valeronitriles for the synthesis of epothilones and epothilone derivatives and process for the production of these new intermediate products in the synthesis and the use for the production of epothilones or epothilone derivatives.

  该发明涉及用于合成依托利酮和依托利酮衍生物的3,5-二羟基-2,2-二甲基-戊腈，以及用于在合成过程中生产这些新中间产物的方法，以及用于生产依托利酮或依托利酮衍生物的用途。
• Transition-metal-free stereoselective synthesis of C(1)–C(6) fragment of epothilones and their structural analogues
  作者：Denis G. Shklyaruck、Artsiom N. Fedarkevich、Yurii Yu. Kozyrkov

  DOI：10.1016/j.tet.2016.10.038

  日期：2016.12

  Two efficient and scalable asymmetric syntheses of C(1)–C(6) fragment of epothilones and their structural analogues from commercially available 1,2:5,6-di-O-isopropylidene-d-mannitol have been performed in seven and 12 steps with 35% and 36% overall yields, respectively. Both the approaches include of one-pot, sequential transformations. The key steps are l-histidine-catalyzed aldol reaction, Barton–McCombie

  从商购的1,2- C（1）-C（6）埃坡霉素的片段和它们的结构类似物中的两个有效和可伸缩不对称合成：5,6-二- ö异亚丙基d -mannitol在七个和12已经进行了分别获得35％和36％的总收益。两种方法都包括一锅法，顺序变换。关键步骤是l-组氨酸催化的羟醛反应，Barton-McCombie脱氧，锌介导的Vasella片段化和氧化腈合成。
• C1-C6-epothilone fragments and process for the production of C1-C6-fragments of epothilones and derivatives thereof
  申请人：Schering AG

  公开号：US20030176710A1

  公开（公告）日：2003-09-18

  This invention describes C 1 -C 6 -epothilone fragments and an efficient process for the production of C 1 -C 6 -fragments of epothilones and derivatives thereof.

  这项发明描述了C1-C6-依波酮片段以及一种高效的生产依波酮及其衍生物的C1-C6片段的方法。