[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethylene)-(2E,2′E)-bis(2-methyl-3-phenylacrylate)

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethylene)-(2E,2′E)-bis(2-methyl-3-phenylacrylate)
• 英文别名: [[(4R,5R)-2,2-dimethyl-5-[[(E)-2-methyl-3-phenylprop-2-enoyl]oxy-diphenylmethyl]-1,3-dioxolan-4-yl]-diphenylmethyl] (E)-2-methyl-3-phenylprop-2-enoate
• 化学式: C₅₁H₄₆O₆
• 分子量: 754.923
• InChiKey: DCDITOZRUMWJAO-HVGLSTKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 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-diyl]bis(diphenylmethylene)-(2E,2′E)-bis(2-methyl-3-phenylacrylate) 、 二丁基二氯化锡 、 dibutylstannane 在 NCC(CH₃)2NNC(CH₃)2CN 作用下， 以 甲苯 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis and Some Properties of New Chlorodiorganotin-Substituted Macrodiolides

  摘要：

  Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (4-7) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltin-substituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full H-1, C-13, and Sn-119 data are also reported.

  DOI：

  10.1021/om200987t
• 作为产物：
  描述：

  (E)-2-methyl-3-phenylacryloyl chloride 、 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以57%的产率得到[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethylene)-(2E,2′E)-bis(2-methyl-3-phenylacrylate)
  参考文献：
  名称：

  TADDOL单不饱和酯和双不饱和酯的合成

  摘要：

  报道了(4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇(TADDOL)的十四种新型单酯和二酯的合成. 该研究表明，在正丁基锂 (BuLi) 的存在下，TADDOL (1) 与酰氯（衍生自正常和 α,β-不饱和羧酸）的酯化反应可以生成相应的单酯和二酯的混合物，即后者的产率更高，并且仅是二酯，这取决于起始酸的结构。这些反应在大多数情况下以良好至极好的总产率 (57-95%) 发生。TADDOL 的二氯衍生物与 α,β-不饱和酸的银盐之间的反应也以良好的收率产生了相应的 TADDOL 不饱和二酯。

  DOI：

  10.1055/s-2005-872123

文献信息

• Synthesis of Unsaturated Diesters of Primary, Secondary and Tertiary Diols Derived from Dimethyl (+)-Tartrate and Galactaric­ Acid
  作者：Jimena Scoccia、Darío C. Gerbino、Victor F. Terraza、Adriana E. Zúñiga、Julio C. Podestá

  DOI：10.1002/ejoc.201300130

  日期：2013.7

  The preparation of symmetrical unsaturated diesters of dioe first was the reaction of mixed anhydrides, obtained from α,β-unsaturated acids and benzoyl chloride, with diols 3 (primary), 5 (secondary), and 7 (primary), i.e., Yamaguchi–SantaLucia's method, however only the symmetrical diacrylates of diols 5 and 7 were obtained quantitatively. In the other ten cases studied the reactions led to mixtures

  二烯的对称不饱和二酯的制备首先是由α,β-不饱和酸和苯甲酰氯得到的混合酸酐与二醇3（初级）、5（次级）和7（初级）反应，即山口-然而，SantaLucia 的方法只能定量获得二醇 5 和 7 的对称二丙烯酸酯。在研究的其他十个案例中，反应导致难以分离的对称和不对称二酯混合物。混合酸酐不与叔二醇 4 (TADDOL) 和 8 反应。在所研究的 12 个案例中，所需对称二酯的平均产率为 54%。发现二醇与不饱和酸酐的酰化是一种极好的方法，可生成二醇 3、5、5 的对称不饱和二酯。7 作为唯一的反应产物，平均产率为 83%。不幸的是，该方法不能应用于衍生自叔二醇 4 (TADDOL) 和 8 的二酯。研究的第三种方法是用 nBuLi 的乙醚溶液制备的醇盐与不饱和酰氯在 –50 °C 下的反应，即，Kaiser-Woodruff 协议。发现这是测试的三种方法中最好的。该方法成功应用于合成衍生自二醇
• Synthesis of Mono- and Diunsaturated Esters of TADDOL
  作者：Liliana Koll、Julio Podestá、Darío Gerbino、Sandra Mandolesi

  DOI：10.1055/s-2005-872123

  日期：——

  higher yield, and to justthe diesters, depending on the structure of the starting acids. These reactions take place in most cases in good to excellent overall yields (57-95%). The reaction between a dichloro derivative of TADDOL and the silver salts of α,β-unsaturated acids also gives the corresponding unsaturated diesters of TADDOL in good yields.

  报道了(4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇(TADDOL)的十四种新型单酯和二酯的合成. 该研究表明，在正丁基锂 (BuLi) 的存在下，TADDOL (1) 与酰氯（衍生自正常和 α,β-不饱和羧酸）的酯化反应可以生成相应的单酯和二酯的混合物，即后者的产率更高，并且仅是二酯，这取决于起始酸的结构。这些反应在大多数情况下以良好至极好的总产率 (57-95%) 发生。TADDOL 的二氯衍生物与 α,β-不饱和酸的银盐之间的反应也以良好的收率产生了相应的 TADDOL 不饱和二酯。
• Stereoselective Synthesis and Some Properties of New Chlorodiorganotin-Substituted Macrodiolides
  作者：Darío C. Gerbino、Jimena Scoccia、Liliana C. Koll、Sandra D. Mandolesi、Julio C. Podestá

  DOI：10.1021/om200987t

  日期：2012.1.23

  Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (4-7) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltin-substituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full H-1, C-13, and Sn-119 data are also reported.
• Toward the cholinesterase inhibition potential of TADDOL derivatives: Seminal biological and computational studies
  作者：Andrea R. Costantino、Nitin Charbe、Yorley Duarte、Margarita Gutiérrez、Ady Giordano、Parteek Prasher、Kamal Dua、Sandra Mandolesi、Flavia C. Zacconi

  DOI：10.1002/ardp.202200142

  日期：2022.11

  family (organophosphates), with several reports indicating an intersection between the pesticide's activity and AD. In this study, various TADDOL derivatives were synthesized and their in vitro activities as AChE/BuChE inhibitors as well as their antioxidant activities were studied. Molecular modeling studies revealed the capability of TADDOL derivatives to bind to AChE and induce inhibition, especially

  阿尔茨海默病 (AD) 是一种以认知技能和记忆力逐渐丧失为特征的退行性神经系统疾病。所涉及的确切发病机制仍未揭示，但一些研究表明涉及一系列不同的酶，强调了该疾病的多因素特征。因此，抑制这些酶是开发 AD 治疗的有力方法，有前景的候选药物包括乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BuChE) 和单胺氧化酶。有趣的是，AChE 是主要农药家族（有机磷酸酯）的目标，有几份报告表明农药的活性与 AD 之间存在交叉。在这项研究中，合成了各种 TADDOL 衍生物，并研究了它们作为 AChE/BuChE 抑制剂的体外活性及其抗氧化活性。分子模型研究揭示了 TADDOL 衍生物与 AChE 结合并诱导抑制的能力，尤其是化合物图2b和3c提供的 IC 50值分别为 36.78 ± 8.97 和 59.23 ± 5.31 µM。实验生物活性和分子模型研究清楚地表明，具有特定立体化学的 TADDOL 衍生物在设计有效的