(R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene | 152187-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene
• 英文别名: (R)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate；(4R)-4-tert-Butyldimethylsilyloxy-2,2,6-trimethylcyclohex-1-enyl trifluoromethanesulfonate；[(4R)-4-[tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 152187-06-9
• 化学式: C₁₆H₂₉F₃O₄SSi
• 分子量: 402.551
• InChiKey: LZTKPWDVTRVEGX-GFCCVEGCSA-N

物化性质

• 沸点：
  365.9±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 在 四(三苯基膦)钯 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol
  参考文献：
  名称：

  立体控制的全合成多官能类胡萝卜素，peridinin

  摘要：

  从浮游藻藻鞭毛藻中分离到的芹素是一种高度氧化的类胡萝卜素，在主共轭多烯链上除两端均具有功能化的环己烷环外，还具有烯丙酸和特色（Z）-γ-亚萘丁烯内酯功能。分子。我们通过在精确反应条件下进行Sharpless不对称环氧化，与硅烷基呋喃甲基化物进行Wittig反应，随后进行光敏加氧，立体控制的Pd催化一锅（Z）-γ-亚苯基丁烯内酯合成以及经过修饰的Julia-Kocienski烯化反应，实现了peridinin的立体控制全合成。该合成是控制多官能烯丙基类胡萝卜素的立体化学的第一个实例。

  DOI：

  10.1021/jo048852v
• 作为产物：
  描述：

  (4R*,6R*)-2,2,6-Trimethyl-4-hydroxycyclohexan-1-one 在 咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene
  参考文献：
  名称：

  Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner–Wadsworth–Emmons condensation

  摘要：

  两个对称的C₇,C₈-炔基类胡萝卜素已经通过使用C₁₀-二甲醛和C₁₅-磷酰化物的双向霍纳-沃兹沃斯-埃蒙斯缩合反应立体选择性地制备出来了。

  DOI：

  10.1039/c4ob02144d

文献信息

• Syntheses of allene-modified derivatives of peridinin toward elucidation of the effective role of the allene function in high energy transfer efficiencies in photosynthesis
  作者：Takayuki Kajikawa、Kazuyoshi Aoki、Ram Shanker Singh、Takashi Iwashita、Toshiyuki Kusumoto、Harry A. Frank、Hideki Hashimoto、Shigeo Katsumura

  DOI：10.1039/b907456b

  日期：——

  Peridinin is known as the main light-harvesting pigment in photosynthesis in the sea and exhibits exceptionally high energy transfer efficiencies to chlorophyll a. This energy transfer efficiency is thought to be related to the intricate structure of peridinin, which possesses allene and ylidenbutenolide functions in the polyene backbone. There are, however, no studies on the relationship between the structural features of peridinin and its super ability for energy transfer. We then focused on the subjects of why peridinin possesses a unique allene group and how the allene function plays a role in the exceptionally high energy transfer. Toward elucidation of the exact role of the allene function, we now describe the syntheses of three relatively unstable allene-modified derivatives of peridinin along with the results of the Stark spectroscopy of peridinin and the synthesized peridinin derivatives.

  多甲藻黄素是海洋中光合作用的主要光捕获色素，并且表现出极高效地向叶绿素a转移能量的特性。人们认为这种能量转移效率与多甲藻黄素的复杂结构有关，它在多烯骨架中具有丙二烯和亚乙烯基丁内酯官能团。然而，目前尚无关于多甲藻黄素结构特征与其超强能量转移能力之间关系的研究。因此，我们随后关注了多甲藻黄素为什么具有独特的丙二烯基团以及丙二烯官能团如何在极高能量转移中发挥作用的问题。为了明确丙二烯官能团的确切作用，我们目前描述了三种相对不稳定的多甲藻黄素丙二烯改性衍生物的合成，以及多甲藻黄素和合成衍生物的斯塔克光谱学结果。
• [EN] COMPOUNDS AND METHODS FOR PROMOTING PLANT GROWTH<br/>[FR] COMPOSÉS ET PROCÉDÉS PERMETTANT DE FAVORISER LA CROISSANCE DES PLANTES
  申请人：UNIV KING ABDULLAH SCI & TECH

  公开号：WO2021079356A1

  公开（公告）日：2021-04-29

  Disclosed herein are compounds and methods for promoting plant growth. Formulations containing one or more disclosed compounds or salts thereof, and one or more excipients are disclosed. The formulation adjuvant can be a solid carrier, a liquid carrier, or a surface-active agent. Methods for promoting plant growth typically includes applying one or more formulations to a plant, a plant part, or a growing site of plant. The plant can be a cereal, grain, or vegetable plant. The plant part can be seed or seedling of a plant. The growing site of plant can be soil before, during, or after the plant is planted or a growing medium. In some embodiments, the one or more compounds or salts thereof in the one or more formulations are in an effective amount to decrease biosynthesis and release of strigolactone plant hormones from the plant.

  本文披露了一些用于促进植物生长的化合物和方法。披露了含有一种或多种上述化合物或其盐以及一种或多种赋形剂的配方。该配方助剂可以是固体载体、液体载体或表面活性剂。促进植物生长的方法通常包括将一种或多种配方施用于植物、植物部位或植物的生长场地。植物可以是谷物、粮食或蔬菜植物。植物部位可以是植物的种子或幼苗。植物的生长场地可以是植物种植前、种植期间或种植后的土壤或生长介质。在某些实施例中，一种或多种配方中的一种或多种化合物或其盐的含量足以降低植物中异激素赤霉素的生物合成和释放。
• Synthesis of enantiopure C₃- and C₄-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis
  作者：Marta Domínguez、Rosana Álvarez、Emma Borràs、Jaume Farrés、Xavier Parés、Angel R. de Lera

  DOI：10.1039/b514273c

  日期：——

  (R)-all-trans-3-hydroxyretinal 1, (S)-all-trans-4-hydroxyretinal 3 and (R)-all-trans-4-hydroxyretinal 5 have been synthesized stereoselectively by Horner–Wadsworth–Emmons and Stille cross-coupling as bond-forming reactions. The CBS method of ketone reduction was used in the enantioface-differentiation step to provide the precursors for the synthesis of the 4-hydroxyretinal enantiomers. The kinetic constants of Xenopus laevis ADH8 with these retinoids have been determined.

  (R)-全反式-3-羟基视黄醛 1、(S)-全反式-4-羟基视黄醛 3 和(R)-全反式-4-羟基视黄醛 5 是通过 Horner-Wadsworth-Emmons 和 Stille 交叉偶联作为成键反应立体选择性合成的。在对映体分离步骤中采用了 CBS 酮还原法，为 4-羟基视黄醛对映体的合成提供了前体。已测定了爪蟾 ADH8 与这些视黄酸的动力学常数。
• The Stille Reaction in the Synthesis of the C₃₇-Norcarotenoid Butenolide Pyrrhoxanthin. Scope and Limitations
  作者：Belén Vaz、Marta Domínguez、Rosana Álvarez、Angel R. de Lera

  DOI：10.1021/jo060490z

  日期：2006.8.1

  The sequential Stille cross-coupling reactions of the dihalogenated γ-alkylidenebutenolide 7 with stannanes 9 and 6 afforded the carbon skeleton of pyrrhoxanthin, a highly functionalized C7‘−C8‘ acetylenic C37-norcarotenoid butenolide. Although the first halogen-selective Stille coupling takes place in 90% yield at ambient temperature, double isomerization of the Z,E- to the E,Z-C7‘−C10‘ enyne, likely

  二卤代γ-亚烷基丁烯内酯7与锡烷9和6的顺序Stille交叉偶联反应提供了吡咯黄质的碳骨架，一种高度功能化的C7'-C8'炔属C 37-类胡萝卜素丁烯内酯。尽管第一个卤素选择性Stille偶联在室温下以90％的收率进行，但Z，E-可能由催化剂诱导的E，Z -C7'-C10'烯炔的二次异构化伴随着键的形成，导致9' ž - 20，并最终到9' ž -pyrrhoxanthin 9' ž - 1。
• Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins
  作者：Nasri Nesnas、Robert R Rando、Koji Nakanishi

  DOI：10.1016/s0040-4020(02)00667-1

  日期：2002.8

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.