(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbohydrazide | 1374018-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbohydrazide
• CAS: 1374018-87-7
• 化学式: C₇H₁₄N₄O₄
• 分子量: 218.213
• InChiKey: DZFOOLUNMLHDTE-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbohydrazide 、 氧化双(4-苯基异氰酸酯) 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到(4R,5R,25R,26R)-tetra-(hydrazinecarboxamide)cyclophane
  参考文献：
  名称：

  Synthesis of novel chiral tetra-(hydrazinecarboxamide) cyclophane macrocycles

  摘要：

  A novel class of chiral enantiomerically pure C-2-symmetric polyamide macrocycles has been synthesized from the reaction of chiral dioxolane dicarbohydrazides, obtained from commercially available tartaric acid, and aromatic diisocyanates. The novel macrocycles form in almost quantitative yields in a chemoselective [2+2]-cyclocondensation reaction under conformational bias of the dicarbohydrazides. The reaction takes place in anhydrous THF at a relatively high concentration of reactants without addition of external templates or application of high dilution conditions. The structures of the novel polyamide macrocycles were verified and fully assigned by H-1 NMR, C-13 NMR, 2D ROESY NMR, 2D HMBC, 2D HMQC, DEPT 135, FT IR, and CD spectroscopy. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.05.085
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 肼 作用下， 以 异丙醇 为溶剂， 反应 168.0h， 生成 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbohydrazide
  参考文献：
  名称：

  酒石酸衍生的N-烷基二碳酰肼的合成及对Cu2+离子的配位能力

  摘要：

  从 (R,R)-酒石酸开始，我们通过两种通用方法合成了八种 N-和 N,N-(二-) 烷基二碳酰肼 3 和 4，它们能够形成两种 M2L 和 ML 复合物。这些目标化合物进一步用作配位Cu 2+ 离子的模型氮配体。虽然第一类配合物的形成线性依赖于附加烷基的给电子能力的增加，但 ML 配合物受到所用烷基的电子和空间效应的显着影响。这些观察结果得到了两种复杂类型的理论计算的支持。目标化合物也被用作亨利反应的不对称形式中的手性氮配体。在每个末端氮原子上带有一个甲基的配体 3a 获得了适度的化学产率和低对映选择性。还评估了结构 - 性能关系以获得用于不对称反应的配体设计靶向催化剂的有用指南。

  DOI：

  10.3998/ark.5550190.0013.904

文献信息

• Synthesis of enantiomerically pure macrolides with hydrazide fragments from tetrahydropyran and l-(+)-tartaric acid derivatives
  作者：G. Yu. Ishmuratov、M. P. Yakovleva、G. R. Mingaleeva、M. A. Shutova、R. R. Muslukhov、E. M. Vyrypaev、A. G. Tolstikov

  DOI：10.1007/s11172-013-0032-2

  日期：2013.1

  useful bicyclic 26- and 33-membered macrolides containing 1,3-dioxolane and hydrazide fragments was developed starting from tetrahydropyran via a [1+1]-condensation of 7′-oxooctyl-7-oxooctanoate and bis(7-oxooctyl)hexanedioate with hydrazide of L-(+)-tartaric acid acetonide derivative.

  从四氢吡喃开始，通过 7'-氧辛基-7-氧辛酸酯和双（7）的 [1+1]-缩合，合成了两种可能有用的双环 26 和 33 元大环内酯，其中含有 1,3-二氧戊环和酰肼片段。 -氧辛基)己二酸酯与L-(+)-酒石酸丙酮化物衍生物的酰肼。
• Synthetic Approaches to Optically Active Macrolides Containing Hydrazide Fragments of L-(+)-Tartaric Acid from (+)-3-Carene, (+)-α-Pinene, and S-(–)-Limonene
  作者：G. Yu. Ishmuratov、M. P. Yakovleva、M. A. Shutova、R. R. Muslukhov、N. M. Ishmuratova、A. G. Tolstikov

  DOI：10.1007/s10600-014-1046-1

  日期：2014.10

  An optically pure macrolide containing 1,3-dioxolane, gem-dimethylcyclopropyl, and hydrazide fragments was synthesized from (+)-3-carene via [1+1]-condensation of the product from sequential ozonolysis—reduction and Tishchenko disproportionation of (3S,4S)-[(3R,4R)-4-isopropyl-3-methyl-6-oxoheptyl]-4-isopropyl-3-methyl-6-oxoheptanoate with the hydrazide of L-(+)-tartaric acid acetonide.

  一种光学纯的大环内酯，含有1,3-二氧戊环、宝石-二甲基环丙基和酰肼片段，由（+）-3-蒈烯通过（3S,4S）-（（3R,4R）-4-异丙基-3-甲基-6-氧代庚基）-4-异丙基-3-甲基-6-氧代庚酸乙酰肼与L-（+）-酒石酸乙酰肼的顺序臭氧分解-还原和季申科歧化反应的产物通过[1+1]缩合合成。
• An expedient synthesis and conformational features of acylhydrazone macrocycles derived from tartaric acid: evidence of water and π aromatic hydrogen bond interactions
  作者：Paweł Skowronek、Monika Kuncewicz、Małgorzata Brzostowska、Agnieszka Janiak、Urszula Rychlewska、Jacek Gawroński

  DOI：10.1016/j.tetasy.2012.02.010

  日期：2012.2

  Tartaric acid dihydrazides with acetal protected hydroxy groups react with terephthalaldehyde to preferentially form [2+2] bisacylhydrazone macrocycles. The structures of these macrocycles display all anti N-N and C=N bonds. Both trans- and cis-C(O)-NH bonds are present in the macrocycle thus allowing the formation of a rather compact macrocyclic structure. The structures of the acylhydrazone macrocycle are shown to be different in the crystal and in the isolated molecule due to the structure determining role of water included in the crystal lattice: in the former all of the O=C-C-H bonds are anti, while in the latter both syn- and anti-bonds are present. Both the non-planarity of the bisacylhydrazone molecules and their chiral interchromophoric interactions contribute to the rotatory power of the molecule. The low-temperature X-ray crystal structure of this compound provides direct evidence for hydrogen bonding between water and the aromatic pi-electrons in the solid state. (C) 2012 Elsevier Ltd. All rights reserved.