(S)-Sulforaphane | 155320-20-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (S)-Sulforaphane
• 英文别名: (S)-4-methylsulfinylbutyl isothiocyanate；L‐sulforaphane；sulforaphane；(R)-4-methanesulfinyl-butyl isothiocyanate；(R)-(4-Isothiocyanato-butyl)-methyl-sulfoxid；1-isothiocyanato-4-[(S)-methylsulfinyl]butane
• CAS: 155320-20-0
• 化学式: C₆H₁₁NOS₂
• 分子量: 177.291
• InChiKey: SUVMJBTUFCVSAD-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-Sulforaphane 在 水 、 silver(l) oxide 作用下， 生成 N,N'-bis-(4-methanesulfinyl-butyl)-urea
  参考文献：
  名称：

  硫磺素族的竞争性和光化学性的合成

  摘要：

  萨默·冯·拉潘纳斯·德·萨默斯·沃尔科门德·萨尔芬芬，达斯·L-磺胺芬，德森·安迪波德和达斯·D，萨尔·芬拉芬Wurden合成。Zwischenprodukte der可以合成4-甲基-亚磺酰氧基-正丁基胺的光阻剂和自由基。L-4-甲基亚磺酰正丁基氨基丁香醛Harnstoffderivat

  DOI：

  10.1002/hlca.19480310608
• 作为产物：
  描述：

  (R)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide 在 sodium azide 、 氢氟酸 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.5h， 生成 (S)-Sulforaphane
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016

文献信息

• HPLC Separation of Sulforaphane Enantiomers in Broccoli and Its Sprouts by Transformation into Diastereoisomers Using Derivatization with (<i>S</i>)-Leucine
  作者：Makiko Okada、Atsushi Yamamoto、Sen-ichi Aizawa、Atsushi Taga、Hiroyuki Terashima、Shuji Kodama

  DOI：10.1021/acs.jafc.6b04966

  日期：2017.1.11

  Racemic sulforaphane, which was derivatized with (S)-leucine (l-leucine), was resolved by reversed phase HPLC with UV detection. The optimum mobile phase conditions were found to be 10 mM citric acid (pH 2.8) containing 22% methanol at 35 °C using detection at 254 nm. Sulforaphane enantiomers in florets and stems of five brands of broccoli and leaves and stems of three brands of broccoli sprouts were

  用（S）-亮氨酸（1-亮氨酸）衍生化的消旋萝卜硫烷通过具有UV检测的反相HPLC进行拆分。通过在254 nm处检测，发现最佳流动相条件是在35°C下含有22％甲醇的10 mM柠檬酸（pH 2.8）。用拟议的HPLC方法分析了五种花椰菜小花和茎中的萝卜硫素对映体，以及三种花椰菜芽的叶和茎中的萝卜硫素对映体。在所有样品中都检测到了两种萝卜硫烷对映体。西兰花样品中萝卜硫素的S / R比值，小花为1.5–2.6 / 97.4–98.5％，茎为5.0–12.1 / 87.9–95.0％。该小号/ ř花椰菜芽样品中的比率高于花椰菜样品中的比率，叶子的比率为8.3–19.7 / 80.3–91.7％，茎的比率为37.0–41.8 / 58.2–63.0％。通过分别使用带有手性柱的HPLC（Chiralpak AD-RH）和质谱分别鉴定出西兰花及其新芽样品中检测到的（S）-萝卜硫素。
• Biotransformation of organic sulfides. Part 7. Formation of chiral isothiocyanato sulfoxides and related compounds by microbial biotransformation
  作者：Herbert L. Holland、Frances M. Brown、Brett G. Larsen、Mirjana Zabic

  DOI：10.1016/0957-4166(95)00200-9

  日期：1995.7

  The fungi Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613 have been used for the biotransformation of a series of isothiocyanatoalkyl methyl sulfides and their synthetic precursors, ω-(methylthio)alkylphthalimides. H. species gave predominantly (S) sulfoxides in all cases; M. isabellina gave (R) isothiocyanatoalkyl methyl sulfoxides, but in the case of two ω-(methylthio)alkylphthalimides

  真菌Helminthosporium种类NRRL 4671和伊莎贝拉莫氏菌ATCC 42613已用于一系列异硫氰酸根合烷基甲基硫化物及其合成前体ω-（甲硫基）烷基邻苯二甲酰亚胺的生物转化。^ h。在所有情况下，这些物种主要产生（S）亚砜；伊萨贝利纳霉（M. isabellina）得到（R）异硫氰酸根合烷基甲基亚砜，但在两个ω-（甲硫基）烷基邻苯二甲酰亚胺的情况下，亚砜基本转化为砜，导致前者以（S）构型分离。对先前报道的两种生物转化产物的结构进行了更正（Tetrahedron：不对称，1994年，5，1129）。
• Preparation of (R)-sulforaphane by biotransformation using Helminthosporium species NRRL 4671
  作者：Herbert L. Holland、Frances M. Brown、Brett G. Larsen

  DOI：10.1016/0957-4166(94)80137-1

  日期：1994.7

  The fungus Helminthosporium species NRRL 4671 oxidizes 1-isothiocyanato-4-(methylthio)butane to (-)-1-isothiocyanato-(4R)-(methylsulfinyl)butane (sulforaphane). Helminthosporium also converts 1-methylthio-4-(N-phthalimidyl)butane to the (R) sulfoxide.
• Synthesis of (R)-Sulforaphane Using [cpru(R, R)-CHIRAPHOS)]+ as Chiral Auxiliary
  作者：Wolfdieter A. Schenk、Michael Dürr

  DOI：10.1002/chem.19970030510

  日期：1997.5

  AbstractA new enantioselective (80% ee) synthesis of (R)‐sulforaphane and its epimer (S)‐sulforaphane is described, which makes use of the pseudo‐tetrahedral complex fragment [CpRu‐(CHIRAPHOS)]+ as a chiral auxiliary. Reaction of the chloride complexes [CpRu(L–L)Cl] [L–L = 1,‐bis(diphenylphosphino)ethane (dppe), (2S,3S)‐and (2R,3R)‐bis(diphenylphosphino)‐butane ((S,S)‐ and (R, R)‐CHIRAPHOS, respectively)] with phthalimidobutyl methyl sulfide gives the thioether complexes [CpRu(L–L)(MeSC4H8NPhth)]PF6. Oxygen transfer from dimethyldioxirane (DMD) produces the corresponding sulfoxide complexes in high yield and high diastereoselectivity. Cleavage of the phthaloyl group with aqueous hydrazine and subsequent reaction with thiophosgene yields the sulforaphane complexes [CpRu(L–L)(MeS(O)C4H8NCS)]PF6. Treatment of these with sodium iodide finally liberates the sulforaphane without noticeable racemization.